Ethanol → HCID 13501904, 화합물

HRID 615659

반응식

HRID 615659 반응식
[C:1]([NH:9][CH:10]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:11]([S:14]CC1C=CC(OC)=CC=1)[CH:12]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][C@H:32]([C:34]([N:36]1[CH2:47][CH2:46][CH2:45][C@H:37]1[C:38]([O:40]C(C)(C)C)=[O:39])=[O:35])[CH3:33].C(O)C.C([BH3-])#N.[Na+]>O1CCCC1>[C:1]([NH:9][C@@H:10]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:11]([SH:14])[CH2:12][NH:31][C@H:32]([C:34]([N:36]1[CH2:47][CH2:46][CH2:45][C@H:37]1[C:38]([OH:40])=[O:39])=[O:35])[CH3:33])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 12939800tert-Butyl L-alanyl-L-prolinateHCID 56630203HCID 56630203, 화합물

생성물 1

HCID 13501904HCID 13501904, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (S)-β-(benzoylamino)-α-[[(4-methoxyphenyl)methyl]thio]-benzenebutanal (isomer A) (0.45 g., 1.07 mmole), L-alanyl-L-proline, 1,1-dimethylethyl ester (0.78 g., 3.21 mmole), and crushed 3A° molecular sieves (2 g.) in tetrahydrofuran (5 ml.) and absolute ethanol (5 ml.) is stirred at room temperature under argon. After 2.5 hours, sodium cyanoborohydride (0.20 g., 3 eq.) is added and stirring continued for 15 hours. The reaction mixture is filtered to remove the sieves and the filtrate is diluted with ethyl acetate and washed with water, 1N hydrochloric acid (twice), 1N sodium bicarbonate, and brine. After drying over anhydrous MgSO4, the solvent is removed to give the desired product, as a mixture of diastereomers, as a pale yellow oil. TLC (silica gel, benzene:acetone, 4:1) isomer A at Rf =0.30 and isomer B at Rf =0.13. Flash chromatography (silica gel LPS-1; benzene:acetone, 7:3) affords impure product (isomer A). Repeated flash chromatography (silica gel LPS-1; ethyl acetate:benzene, 6:4) gives 0.20 g. of 1-[N-[(3S)-3-(benzoylamino)- 2-[[(4-methoxyphenyl)methyl]thio]-4-phenylbutyl]L-alanyl]-L-proline, 1,1-dimethylethyl ester (isomer A) as a nearly colorless oil.

후처리

  1. waitcontinued for 15 hours
  2. filtrationThe reaction mixture is filtered
  3. customto remove the sieves
  4. additionthe filtrate is diluted with ethyl acetate
  5. washwashed with water, 1N hydrochloric acid (twice), 1N sodium bicarbonate, and brine
  6. dry with materialAfter drying over anhydrous MgSO4
  7. customthe solvent is removed

출처 및 근거

ORD 기록
ord-c07a68a03f814478b520c6d14dcaaee4
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04500518

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