Propionic Acid → HCID 56615310, 화합물

HRID 1377156노트

반응식

HRID 1377156 반응식
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[CH2:19][CH2:18]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:33]([O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45]I)=[CH:43][CH:42]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(=O)CC>C1COCC1.CCCCCC.C(OCC)(=O)C.O>[CH2:33]([O:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:45][C@@H:19]2[CH2:18][C@@H:17]([C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[O:21][C:20]2=[O:22])=[CH:47][CH:48]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

8

반응물 4

HCID 1032Propionic AcidHCID 2733832Lithium HexamethyldisilazideHCID 10946873(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-oneHCID 11723738p-Benzyloxybenzyl iodide

생성물 1

HCID 56615310HCID 56615310, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 21226206Ethyl acetate hexane용매

실험 절차

In analogy with Example 5d), 5.2 g (16.7 mmol) of 5(S)-[1(S)-(Boc-amino)-2-cyclohexylethyl]-dihydrofuran-2-one [(preparation, see Example 12a)], dissolved in 50 ml of THF, are deprotonated, at -70° C., with 33.4 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated, at -75° C. for 1 h, with 5.2 g (16.07 mmol) of 4-benzyloxybenzyl iodide [preparation, see Example 1d)] in 15 ml of THF. Treating, at -75° C., with 6.2 ml (83.02 mmol) of propionic acid and water, and further working up, affords the title compound after column chromatography (SiO2, hexane/ethyl acetate: 4/1). TLC Rf (hexane/ethyl acetate: 4/1)=0.27; tRet (II)=20.41 min.

후처리

  1. custom[preparation

출처 및 근거

ORD 기록
ord-e79bd312a256491cb4dc99f461e0a132
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663200

반응 노트

불러오는 중…