(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid → (2S)-N-((1S,2S)-3-{(2S,4S)-2-[N-(tert-butyl)carbamoyl]-4-fluoropyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide

HRID 1780252Notes

Reaction equation

HRID 1780252 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:21]([OH:25])[C:22](O)=[O:23])=[O:18])[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([N:40]([C:49]([CH3:52])([CH3:51])[CH3:50])[C:41](=[O:48])[C@@H:42]1[CH2:46][C@H:45]([F:47])[CH2:44][NH:43]1)=O)(C)(C)C>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@H:21]([OH:25])[C:22]([N:43]1[CH2:44][C@@H:45]([F:47])[CH2:46][C@H:42]1[C:41]([NH:40][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:48])=[O:23])=[O:18])[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57125825(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acidHCID 67722513(4S)-N-t-butoxycarbonyl-4-fluoro-N-t-butyl-L-prolinamide

Product 1

HCID 473126(2S)-N-((1S,2S)-3-{(2S,4S)-2-[N-(tert-butyl)carbamoyl]-4-fluoropyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamideYield 39.1%

Procedure

Following a procedure similar to that described in Example 1, but using 222 mg (0,5 mmol) of (2S,3S)-3-(N2 -benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid and 144 mg (0.5 mmol) of (4S)-N-t-butoxycarbonyl-4-fluoro-N-t-butyl-L-prolinamide, 120 mg of the title compound were obtained as a colorless powder, melting at 95°-100° C.

Sources & evidence

ORD record
ord-60c8bc2894e14e68bad70a37f7315f8b
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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