تفاعل #429292

معادلة التفاعل

6

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 5-allyl ester 1-benzyl ester

decanoyl chloride

→

7

المردود 63.5%

2-Decanoylamino-pentanedioic acid 5-allyl ester 1-benzyl ester

المردود 63.5%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe Fmoc protective group was subsequently removed by exposure to DMAP
2. 2
   أخرىto give 2-Decanoylamino-pentanedioic acid 5-allyl ester 1-benzyl ester (7) in 63% yield
3. 3
   workup.STIRRINGstirred for 2 h at 22° C.
4. 4
   استخلاصextracted with saturated sodium bicarbonate solution (2×10 mL)
5. 5
   تجفيفThe organic layer was dried (Na2SO4)
6. 6
   أخرىevaporated to dryness
7. 7
   أخرىthe residue was chromatographed on SiO2 (Hexanes/EtOAc, 5:1)

الإجراء التجريبي

The Fmoc protective group was subsequently removed by exposure to DMAP and the free amine was acylated in situ with decanoyl chloride to give 2-Decanoylamino-pentanedioic acid 5-allyl ester 1-benzyl ester (7) in 63% yield as follows. To a suspension of 1 g (2.0 mmol) of 6 in 10 mL of CH2Cl2 was added 1 g (8.2 mmol) of DMAP. The reaction mixture was stirred at 22° C. for 24 h, treated with 0.62 mL (3.0 mmol) of decanoyl chloride, stirred for 2 h at 22° C., and extracted with saturated sodium bicarbonate solution (2×10 mL). The organic layer was dried (Na2SO4), evaporated to dryness, and the residue was chromatographed on SiO2 (Hexanes/EtOAc, 5:1) to give 548 mg (63%) of 7 as a viscous oil: IR (neat) 3293, 3063, 2924, 2855, 1740, 1649, 1534, 1453, 1379, 1175, 986, 930 cm-1 ; 1H NMR δ 7.26 (s, 5 H), 6.68 (d, I H, J=7.8 Hz), 5.85-5.75 (m, 1 H), 5.22 (d, 1 H, J=17.3 Hz), 5.14 (d, 1 H, J=10.4 Hz), 5.08 (s, 2 H), 4.63-4.57 (m, 1 H), 4.48 (d, 2 H, J=5.6 Hz), 2.38-2.28 (m, 2 H), 2.2-2.1 (m, 3 H), 2.0-1.9 (m, 1 H), 1.55 (t, 2 H, J=6.9 Hz), 1.20 (bs, 12 H), 0.82 (t, 3 H, J=5.9 Hz); 13C NMR δ 173.0, 172.1, 171.6, 135.0, 131.7, 128.2, 128.1, 127.8, 117.9, 66.8, 64.9, 51.3, 36.0, 31.6, 29.9, 29.1, 29.0, 26.8, 25.3, 22.3, 13.8; MS (El) m/z (relative intensity) 431 (12), 319 (21), 296 (51), 142 (100), 124 (31), 91 (91); HRMS (El) m/z calculated for C25H37NO5 : 431.2672, found: 431.2673.

المصدر