Methanol → HCID 13343641, compound

HRID 1263217Notes

Reaction equation

HRID 1263217 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[C:5]=1[C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:27][CH2:26][CH2:25][C@H:14]1[C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:12])[CH3:10])=[O:7])([OH:3])=[O:2].[OH-].[Na+].CO>O>[C:1]([C:4]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[C:5]=1[C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:27][CH2:26][CH2:25][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH3:10])=[O:7])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 131713563HCID 131713563, compound

Product 1

HCID 13343641HCID 13343641, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ester product from part (b) (1 g., 2.1 mmole) is stirred in a 10% sodium hydroxide and methanol solution at room temperature for 2.5 hours. The reaction solution is diluted with water and washed with ethyl ether. Upon acidification of the aqueous phase with 10% hydrochloric acid and saturation with sodium chloride, the diacid is extracted via multiple extractions into ethyl acetate. After drying (MgSO4) and evaporating, 0.5 g. of product is obtained as a white solid. In order to remove entrapped solvent, 300 mg. of material is dissolved in water and lyophilized to give pure 1-[N-(2-carboxy-6-nitrobenzoyl)-L-alanyl]-L-proline as a white solid; m.p. 134°-137°. TLC (silica gel Rf =0.28, ethyl acetate:pyridine:acetic acid:water; 45:20:6:11). [α]D =-57.2 (c=1.0, methanol).

Workup

  1. washwashed with ethyl ether
  2. extractionUpon acidification of the aqueous phase with 10% hydrochloric acid and saturation with sodium chloride, the diacid is extracted via multiple extractions into ethyl acetate
  3. dry with materialAfter drying (MgSO4)
  4. customevaporating
  5. customof product is obtained as a white solid
  6. customIn order to remove
  7. dissolutionof material is dissolved in water

Sources & evidence

ORD record
ord-28f1a534af60413d99f5dd12ac539547
Source dataset
uspto-grants-1984_06
Patent number
US04456595

Reaction notes

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