Sodium Hydroxide → HCID 11385609, compound

HRID 602335Notes

Reaction equation

HRID 602335 reaction equation
[OH-].[Na+].[N+](C1C=CC(C([O:12][C@H:13]2[CH2:17][C@H:16]([C:18](=[O:33])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C:27]4=[O:32])=[CH:22][CH:21]=3)[N:15]([C:34](=[O:43])[NH:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[CH2:14]2)=O)=CC=1)([O-])=O>CO>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([NH:35][C:34]([N:15]2[CH2:14][C@@H:13]([OH:12])[CH2:17][C@@H:16]2[C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][C:27]3=[O:32])=[CH:22][CH:21]=2)=[O:33])=[O:43])=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58691276HCID 58691276, compound

Product 1

HCID 11385609HCID 11385609, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.3 0.075 ml of 1N sodium hydroxide solution is added with ice cooling to the solution of 50 mg (0.082 mmol) of (3S,5R)-1-(4-chlorophenylcarbamoyl)-5-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidin-3-yl 4-nitrobenzoate in 2 ml of methanol, and the reaction mixture is stirred for 15 minutes. The precipitate is filtered off and washed with 2 ml of methanol and dried, giving 35 mg (93%) of 1-N-[(4-chlorophenyl)]-2-N-{[4-(3-oxomorpholin-4-yl)phenyl]}-(2R,4S)-4-hydroxypyrrolidine-1,2-dicarboxamide as colourless crystals, ESI 459, m.p. 243° (decomposition).

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with 2 ml of methanol
  3. customdried

Sources & evidence

ORD record
ord-bc25eea65aad4994a31f69cddf6c6628
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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