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Dicyclohexylcarbodiimide → (2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramide

HRID 986360
Notes
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Reaction equation

HRID 986360 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25].OS1C2C=CC=CC=2N=C1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:10]([OH:14])[C:11]([NH:27][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12206183Isobutylamine HydrochlorideHCID 59490980(2RS, 3S)-3-tert-butoxycarbonylamino-4-cyclohexyl-2-hydroxybutyric acidHCID 178527226HCID 178527226, compound

Product 1

HCID 86741924(2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramideYield 125.8%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 400 mg of the butyric acid compound, 175 mg of isobutylamine hydrochloride, 270 mg of 1-hydroxybenzotiazole and 0.22 ml of triethylamine in 20 ml of ethyl acetate was added 300 mg of dicyclohexylcarbodiimide with stirring under ice-cooling, and then the mixture was still stirred for 16 hours. The reaction mixture was cooled, and filtered to remove insoluble materials. The filtrate was washed successively with an aqueous citric acid solution, a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 595 mg of (2RS, 3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexyl-2-hydroxy-N-isobutylbutyramide.

Workup

  1. temperaturecooling
  2. stirringthe mixture was still stirred for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customto remove insoluble materials
  6. washThe filtrate was washed successively with an aqueous citric acid solution
  7. dry with materiala 5% aqueous sodium bicarbonate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b12e594976c4c188d2d04aad7c54a26
Source dataset
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04711958

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes