Phosphoric Acid → HCID 13132322, compound

HRID 2372599Notes

Reaction equation

HRID 2372599 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12](=[O:43])[CH2:13][N:14]([C:24](=[O:42])[C@H:25]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[NH2:26])[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)([CH3:10])([CH3:9])[CH3:8].C([O-])(=O)C.[Na+].O=[C:50]([CH2:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:51]([O:53][CH2:54][CH3:55])=[O:52].C([BH3-])#N.[Na+].P(=O)(O)(O)O>CO.C(O)(=O)C>[C:7]([O:11][C:12](=[O:43])[CH2:13][N:14]([C:24](=[O:42])[C@H:25]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[NH:26][C@@H:50]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:56][CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[CH:15]1[CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23]1)([CH3:10])([CH3:8])[CH3:9]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 517045Sodium AcetateHCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydride2×HCID 13132297HCID 13132297, compound

Product 1

HCID 13132322HCID 13132322, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

Nε -Carbobenzoxy-L-lysyl-N-(indan-2-yl)glycine tert-butyl ester oxalate (3.5 g) is dissolved in 20 ml of methanol, and 1 g of sodium acetate, 1.2 g of acetic acid, 8 g of molecular sieve and 15 g of ethyl 2-oxo-4-phenyl-butyrate are added. To this mixture is added dropwise with stirring a solution of 3.3 g of sodium cyanoborohydride in 30 ml of methanol over 2 hours. 3 g of sodium cyanoborohydride is further added, and the mixture is stirred for 3 hours. After addition of 200 ml of 25% aqueous phosphoric acid, the reaction mixture is extracted with two 200-ml portions of ethyl acetate. The extract is washed with 0.5 N aqueous sodium hydroxide and with water, and dried over anhydrous magnesium sulfate. The ethyl acetate is distilled off under reduced pressure, and the oil thus obtained is separated and purified by silica gel column chromatography (acetone-benzene (1:12 to 1:5). The first fraction gives 1.1 g of Nα -[1-(R)-ethoxycarbonyl-3-phenylpropyl]-Nε -carbobenzoxy-L-lysyl-N-(indan-2-yl)glycine tert-butyl ester as an oil.

Workup

  1. additionTo this mixture is added dropwise
  2. extractionthe reaction mixture is extracted with two 200-ml portions of ethyl acetate
  3. washThe extract is washed with 0.5 N aqueous sodium hydroxide and with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe ethyl acetate is distilled off under reduced pressure
  6. customthe oil thus obtained
  7. customis separated
  8. custompurified by silica gel column chromatography (acetone-benzene (1:12 to 1:5)

Sources & evidence

ORD record
ord-59aebc5442de4be4a0015aa08d3bb15e
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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