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Morpholine → 4-[(2RS, 3S)-3-(tertbutoxycarbonyl)amino-4-cyclohexyl-2-hydroxybutyryl]morpholine

HRID 986364
Notes
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Reaction equation

HRID 986364 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].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)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]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 59490980(2RS, 3S)-3-tert-butoxycarbonylamino-4-cyclohexyl-2-hydroxybutyric acid

Product 1

HCID 867419274-[(2RS, 3S)-3-(tertbutoxycarbonyl)amino-4-cyclohexyl-2-hydroxybutyryl]morpholine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 200 mg of (2RS, 3S)-3-tertbutoxycarbonylamino-4-cyclohexyl-2-hydroxybutyric acid which was prepared in Reference Example 4, 0.06 ml of morpholine and 13 mg of 1-hydroxybenzotriazole in 6 ml of ethyl acetate was added 150 mg of dicyclohexylcarbodiimide with stirring under ice-cooling, and the mixture was stirred for 16 hours at room temperature. 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 296 mg of 4-[(2RS, 3S)-3-(tertbutoxycarbonyl)amino-4-cyclohexyl-2-hydroxybutyryl]morpholine.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 16 hours at room temperature
  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-128c961c545a4341a85802fcb4e6bc9b
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