تفاعل #83068

ord-a4d1c296c64641c18e536dc8b64f2f38

معادلة التفاعل

O=C(OCc1ccccc1)N1CCN(C(=O)[C@H]2C[C@H](Br)CO2)CC1
product
O=C(OCc1ccccc1)N1CCN(C(=O)[C@H]2C[C@H](Br)CO2)CC1
4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester
CC([O-])=S.[K+]
potassium thioacetate
C1COCCOCCOCCOCCOCCO1
18-crown-6
CC#N
acetonitrile
→
CC(=O)S[C@H]1CO[C@@H](C(=O)N2CCN(C(=O)OCc3ccccc3)CC2)C1
desired product
المردود 82.4%
CC(=O)S[C@H]1CO[C@@H](C(=O)N2CCN(C(=O)OCc3ccccc3)CC2)C1
4-(4-S-Acetyl-2,5-anhydro-3-deoxy-4-thio-L-threo-pentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester
المردود 82.4%

المتفاعلات

O=C(OCc1ccccc1)N1CCN(C(=O)[C@H]2C[C@H](Br)CO2)CC1
product
O=C(OCc1ccccc1)N1CCN(C(=O)[C@H]2C[C@H](Br)CO2)CC1
4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester
CC([O-])=S.[K+]
potassium thioacetate
C1COCCOCCOCCOCCOCCO1
18-crown-6
CC#N
acetonitrile

الكواشف

لا شيء

المذيبات

CCCCCC.CCOC(C)=O
ethyl acetate hexane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

The title compound is prepared by the procedure of Example 139 using 1.14 g of product from Example 151, 0.393 g of potassium thioacetate, 0.1517 g of 18-crown-6 and 10 ml of acetonitrile to give 0.928 g of the desired product after chromatography (silica gel: 10-60% ethyl acetate/hexane).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05623081uspto-grants-1997_04