반응 #86635

반응 방정식

DIPEA

N-BOC-O-allyl-tyrosine

HATU

leucine methyl ester hydrochloride

→

(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid methyl ester

용매

EtOAc

DMF

반응 조건

후처리

1. 1
   기타before being partitioned between EtOAc and 1M hydrochloric acid
2. 2
   세척The organic phase was then washed sequentially with 1M hydrochloric acid and brine
3. 3
   건조before being dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타Purification
7. 7
   세척eluting with a gradient of 1/5 EtOAc/(50/70) petroleum ether to 100% EtOAc
8. 8
   기타to yield a white solid, 8.45 g, 58%

실험 절차

N-BOC-O-allyl-tyrosine (obtained from NeoMPS, San Diego, Calif. 92126, USA) (10.0 g, 32.5 mmol), HATU (12.4 g, 35.8 mmol) and leucine methyl ester hydrochloride (5.90 g, 65.0 mmol) were dissolved in anhydrous DMF (50 mL). DIPEA (22.7 mL, 130 mmol) was added and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The organic phase was then washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/5 EtOAc/(50/70) petroleum ether to 100% EtOAc to yield a white solid, 8.45 g, 58%. Rf=0.33 (1/3 EtOAc/(50/70) petroleum ether).

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