Benzene → tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate

HRID 216291

반응식

HRID 216291 반응식
[NH2:1][CH2:2][C@@H:3]([OH:32])[C@@H:4]([NH:12][C:13](=[O:31])[C@@H:14]([N:18]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[N:25]=[C:26]([CH3:29])[S:27][CH:28]=2)[C:19]1=[O:30])[CH:15]([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C=CC=CC=1.[O:39]([C:44]([N:46]1[CH2:52][CH2:51][CH2:50][C@H:47]1[CH:48]=O)=[O:45])[C:40]([CH3:43])([CH3:42])[CH3:41].[BH4-].[Na+]>C(O)C>[OH:32][C@@H:3]([C@@H:4]([NH:12][C:13](=[O:31])[C@@H:14]([N:18]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[N:25]=[C:26]([CH3:29])[S:27][CH:28]=2)[C:19]1=[O:30])[CH:15]([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:2][NH:1][CH2:48][CH:47]1[CH2:50][CH2:51][CH2:52][N:46]1[C:44]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:45]

참가 물질

6

반응물 4

HCID 241BenzeneHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 4311764Sodium borohydrideHCID 66891621(2S)-N-[(1S,2R)-3-amino-1-benzyl-2-hydroxypropyl]-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanamide

생성물 1

HCID 66891972tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate수율 103%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

A solution of the product of Example 274C (59 mg) in ethanol:benzene (1 mL, 1:1) was treated with N-t-butoxylcarbonyl-(L)-prolinal (26 mg, 1 equivalent), stirred at 70° C. for 1 hour, cooled at 25° C., treated with NaBH4 (14 mg, 3 equivalents) at 25° C. and stirred for 16 hours. The mixture was quenched with saturated NH4Cl and partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated to give 85 mg of the crude title compound.

후처리

  1. temperaturecooled at 25° C.
  2. stirringstirred for 16 hours
  3. customThe mixture was quenched with saturated NH4Cl
  4. custompartitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1f8324259554487484ee94bb8f406dc8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193227B2

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