Citric Acid → HCID 70078830, compound

HRID 1761418Notes

Reaction equation

HRID 1761418 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@@H:21]([C:38]([OH:40])=[O:39])[CH2:22][CH2:23][C:24]([N:26]1[CH:34]2[CH:29]([CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:28][CH:27]1[C:35]([OH:37])=[O:36])=[O:25])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:47][O:48][C:49]1[CH:63]=[CH:62][CH:61]=[CH:60][C:50]=1[CH2:51][O:52]N1C(=O)CCC1=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@@H:21]([C:38]([OH:40])=[O:39])[CH2:22][CH2:23][C:24]([N:26]1[C@@H:34]2[C@@H:29]([CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:28][C@H:27]1[C:35]([OH:37])=[O:36])=[O:25])=[O:19])[NH:17][C:51](=[O:52])[C:50]1[CH:60]=[CH:61][CH:62]=[CH:63][C:49]=1[O:48][CH3:47])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 20044117HCID 20044117, compoundHCID 86742974HCID 86742974, compound

Product 1

HCID 70078830HCID 70078830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S,3aS,7aS)-1-(N6 -benzyloxycarbonyl-L-lysyl-gamma-D-glutamyloctahydro-1H-indole-2carboxylic acid was dissolved in 6 ml of water, and sodium carbonate and 10 ml of THF were added. With vigorous stirring, N-(2-methoxybenzyloxy)succinimide was added. The mixture was stirred overnight at room temperature. The reaction mixture was acidified with 10% citric acid, and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The residue was chromatographed on a column of CHP20P using acetonitrile/water (30%→70% gradient) as an eluent. Fractions containing the desired product were concentrated to dryness under reduced pressure to give 1.0 g of (2S,3aS,7aS)-1-[N6 -benzyloxycarbonyl-N2 -(2-methoxybenzoyl)-L-lysyl-gamma-D-glutamyl]octahydro-1H-indole-2-carboxylic acid.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue was chromatographed on a column
  5. additionFractions containing the desired product
  6. concentrationwere concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c85441444c7e4791895ee53d8fbdd40a
Source dataset
uspto-grants-1989_05
Patent number
US04826814

Reaction notes

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