Methanol → HCID 131722108, compound

HRID 366093Notes

Reaction equation

HRID 366093 reaction equation
C([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C@H:16]([C:33]([NH:35][C@@H:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[CH3:37])=[O:34])[NH:17][C:18](=[O:32])[CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[S:11])(=O)C1C=CC=CC=1.CO.C([O-])([O-])=O.[K+].[K+]>O>[NH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C@H:16]([C:33]([NH:35][C@@H:36]([C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1)[CH3:37])=[O:34])[NH:17][C:18](=[O:32])[CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[S:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 131722107HCID 131722107, compound

Product 1

HCID 131722108HCID 131722108, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-N5 -(Benzoylaminothiocarbonyl)-N2 -(diphenylacetyl)-(R)-N-[1-(4-methoxyphenyl)ethyl]ornithine amide (2.25 g; 3.6 mmol; from step (a) above), methanol (250 mL), water (250 mL) and K2CO3 (1.49 g; 10.8 mmol) were combined and stirred for 24 h at room temperature. The reaction mixture was then partitioned between EtOAc (250 mL) and brine (250 mL). The EtOAc layer was separated and washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 1.86 g (99%) of the sub-title compound as a white foam.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc (250 mL) and brine (250 mL)
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe62babafb8a4b84bcbcdbbdf6eb9868
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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