Water → HCID 86714430, compound

HRID 1750221Notes

Reaction equation

HRID 1750221 reaction equation
[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[C:16]([N+:28]([O-])=O)[CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl.O>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[C:16]([NH2:28])[CH:15]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 86714431HCID 86714431, compound

Product 1

HCID 86714430HCID 86714430, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

140 mg of (S)-2-[4-(2-Chloro-phenylamino)-3-nitro-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester were dissolved in 5 ml ethyl acetate, 342 mg of tin(II)chloride-dihydrate were added and the mixture was stirred at rt for 4 h. Water was added to the reaction. The mixture was filtrated over celite. The pH of the filtrate was adjusted to 7, the layers were separated and the organic layer was extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate and concentrated to yield 103 mg (79%) of (S)-2-[3-Amino-4-(2-chloro-phenylamino)-benzoylamino]-4-methyl-pentanoic acid tert-butyl ester.

Workup

  1. filtrationThe mixture was filtrated over celite
  2. customthe layers were separated
  3. extractionthe organic layer was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-059b8238c4f84cb6b38de72833658b87
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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