Benzyl isocyanate → (S)-2-[[(S)-2-[1-Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

HRID 1720498Notes

Reaction equation

HRID 1720498 reaction equation
C(O[C:6]([N:8]1[CH2:31][CH2:30][CH2:29][C@H:9]1[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:11])=[O:7])(C)(C)C.Cl.O1CCOCC1.[CH2:39]([N:46]=C=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH2:39]([NH:46][C:6]([N:8]1[CH2:31][CH2:30][CH2:29][C@H:9]1[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:11])=[O:7])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 3

HCID 76639Benzyl isocyanateHCID 204431481,4-Dioxane hydrochlorideHCID 22860058(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine

Product 1

HCID 57083169(S)-2-[[(S)-2-[1-Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Procedure

By the same procedure as in Example 21-B), (2S)-1-[N-(t-butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2-(4-methoxyphenoxy) ethyl]pyrrolidine (722 mg) was treated with 4N hydrochloric acid/1,4-dioxane, followed by reaction with benzylisocyanate (0.21 ml) to give 596 mg of the title compound as crystals. C) (2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(4-methoxyphenoxyacetyl)pyrrolidine

Sources & evidence

ORD record
ord-f153fa3f91df48b59afb7a1185259abf
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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