Hydrochloric Acid → HCID 70445877, compound

HRID 2418181Notes

Reaction equation

HRID 2418181 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[C:11]([O:15][C:16](=[O:30])[C@H:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:18][C:19](=[O:22])[CH2:20][NH2:21])([CH3:14])([CH3:13])[CH3:12].C([BH3-])#N.[Na+].Cl.P(=O)(O)(O)O.[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>CO.CCOCC.C(O)C>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[C:11]([O:15][C:16](=[O:30])[C@H:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:18][C:19](=[O:22])[CH2:20][NH:21][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)([CH3:14])([CH3:12])[CH3:13]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 971Oxalic AcidHCID 1004Phosphoric AcidHCID 119832-IndanoneHCID 5003444Sodium cyanoborohydrideHCID 13385086HCID 13385086, compound

Product 1

HCID 70445877HCID 70445877, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-Indanone (3.6 g) and glycyl-L-phenylalanine tert-butyl ester (7.3 g) are dissolved in 50 ml of methanol and 3 g of sodium cyanoborohydride is added in small portions at room temperature. Then, 0.5 ml of ethanolic solution of 7N hydrogen chloride (0.5 ml) is added dropwise and the mixture is allowed to stand at room temperature overnight. To the reaction mixture are added 50 ml of methanol and 200 ml of 10% phosphoric acid, followed by extraction with a mixture of ether (100 ml) and petroleum ether (100 ml). The aqueous layer is made neutral with sodium hydrogen carbonate and extracted twice with 200 ml portions of ethyl acetate. The extracts are combined, dried over anhydrous magnesium sulfate, and distilled to remove the solvent, whereby a yellow-colored oil is obtained. This product is dissolved in ether and a solution of 2 g of oxalic acid in a small quantity of ethanol is added. The resulting crystalline precipitate is collected by filtration and dried to give 5.4 g of N-(2-indanyl)glycyl-L-phenylalanine tert-butyl ester oxalate. The product is added to a mixture of 20 ml of methanol and 100 ml of water and made alkaline by dropwise addition of 1N sodium hydroxide with stirring. The crystalline precipitate is collected by filtration and dried to give 4 g of free N-(2-indanyl)glycyl-L-phenylalanine tert-butyl ester melting at 117°-120° C.

Workup

  1. extractionfollowed by extraction with a mixture of ether (100 ml) and petroleum ether (100 ml)
  2. extractionextracted twice with 200 ml portions of ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent, whereby a yellow-colored oil
  6. customis obtained
  7. filtrationThe resulting crystalline precipitate is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d62eec7fa4864f7fa9fdd17fd1b2e397
Source dataset
uspto-grants-1984_09
Patent number
US04472383

Reaction notes

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