Boc-Hyp-NH-tBu → (2S)-N-((1S,2S)-3-{(5S,3R)-5-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide

HRID 1780237Notes

Reaction equation

HRID 1780237 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]([OH:24])=O)=[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]1[CH2:51][C@H:50]([OH:52])[CH2:49][C@H:41]1[C:42]([NH:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=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:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:21]([OH:25])[C:22]([N:40]1[CH2:51][C@H:50]([OH:52])[CH2:49][C@H:41]1[C:42]([NH:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:24])=[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 10334194Boc-Hyp-NH-tBuHCID 57125825(2S,3S)-3-(N2-benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid

Product 1

HCID 473122(2S)-N-((1S,2S)-3-{(5S,3R)-5-[N-(tert-butyl)carbamoyl]-3-hydroxypyrrolidinyl}-2-hydroxy-3-oxo-1-benzylpropyl)-3-carbamoyl-2-[(phenylmethoxy)carbonylamino]propanamide

Procedure

A procedure similar to that described in Example 1 was repeated, except that (2S,3S)-3-(N2 -benzyloxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyric acid (prepared as described in Preparation 1) and (4R)-1-t-butoxycarbonyl-N-t-butyl-4-hydroxy-L-prolinamide (prepared as described in Preparation 5) were used as starting materials, in relative proportions similar to those used in that Example, to obtain the title compound as colorless powdery crystals, melting at 115°-120° C.

Sources & evidence

ORD record
ord-cd45bbd63aff4101bf9319924a423471
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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