Potassium Hydroxide → HCID 15788472, compound

HRID 976000Notes

Reaction equation

HRID 976000 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:36])[CH2:20][NH:21][C:22](=[O:35])[NH:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([O:33]C)=[O:32])[CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO.O>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:36])[CH2:20][NH:21][C:22](=[O:35])[NH:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([OH:33])=[O:32])[CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57240898HCID 57240898, compound

Product 1

HCID 15788472HCID 15788472, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The operation is carried out as in Example 9, but starting from 1.9 g of methyl (2S,5R)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetate in solution in 60 cm3 of methanol and 0.22 g of potassium hydroxide dissolved in 30 cm3 of water. After treatment, 0.65 g of (2S,5R)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetic acid, melting at 112° C., [α]D20 =+30.6°±0.8° (c=1; methanol) is obtained.

Sources & evidence

ORD record
ord-1a13ccc346a54ae1b05f18b4ba25d598
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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