Diphosgene → (2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine

HRID 1720518Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.ClC(OC(Cl)(Cl)Cl)=O.C([O:22][C:23]([N:25]1[CH2:46][CH2:45][CH2:44][C@H:26]1[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH:34]([OH:43])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:28])=O)(C)(C)C>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:23]([N:25]2[CH2:46][CH2:45][CH2:44][C@H:26]2[C:27]([N:29]2[CH2:33][CH2:32][CH2:31][C@H:30]2[CH:34]([OH:43])[CH2:35][O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:28])=[O:22])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 10426Diphosgene

HCID 660364-Chlorobenzylamine

HCID 70050944(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine

Product 1

HCID 67771673(2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidineYield 48.4%

Procedure

By the same procedure as in Example 28-B), while using 4-chlorobenzylamine (0.71 g), trichloromethyl chloroformate (0.3 ml) and (2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (2.00 g), there was obtained 1.13 g of the title compound.

Sources & evidence

ORD record: ord-b1327d7cdcd14a29acefcd7dbf2ff3df
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506256

Reaction notes

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