tert-butyl N-[[(2S,3S)-3-[[(2S)-4-amino-4-oxo-2-(quinoline-2-carbonylamino)butanoyl]amino]-2-hydroxy-4-phenyl-butyl]-benzyl-amino]carbamate → 1-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenylbutyl]-1-[phenylmethyl]-hydrazine

HRID 1291797Notes

Reaction equation

HRID 1291797 reaction equation
[OH:1][C@H:2]([C@@H:20]([NH:28][C:29](=[O:48])[C@H:30]([CH2:44][C:45](=[O:47])[NH2:46])[NH:31][C:32]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1)=[O:33])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O>C(O)=O>[OH:1][C@H:2]([C@@H:20]([NH:28][C:29](=[O:48])[C@H:30]([CH2:44][C:45](=[O:47])[NH2:46])[NH:31][C:32]([C:34]1[CH:43]=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1)=[O:33])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:5]

Participants

3

Reactant 1

HCID 491700tert-butyl N-[[(2S,3S)-3-[[(2S)-4-amino-4-oxo-2-(quinoline-2-carbonylamino)butanoyl]amino]-2-hydroxy-4-phenyl-butyl]-benzyl-amino]carbamate

Product 1

HCID 697828951-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenylbutyl]-1-[phenylmethyl]-hydrazine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1.0 g (1.53 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[phenylmethyl]-2-[tert-butoxycarbonyl]-hydrazine (Example 100 B) is dissolved in 10 ml of formic acid under protective gas and stirred for 16 h at RT. The formic acid is removed by evaporation under HV, the residue is partitioned between 3 portions of ethyl acetate, saturated NaHCO3 solution and brine, and the organic phases are dried with Na2SO4 and concentrated by evaporation to yield the title compound: tRet (V)=10.7 min.

Workup

  1. customThe formic acid is removed by evaporation under HV
  2. customthe residue is partitioned between 3 portions of ethyl acetate, saturated NaHCO3 solution and brine
  3. dry with materialthe organic phases are dried with Na2SO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b8680e366a4d426cae6e78f44d5151eb
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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