Ammonia → HCID 14390816, compound

HRID 1112085Notes

Reaction equation

HRID 1112085 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13](O)=[O:14])[CH2:3][S:4][CH2:5][C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1.C([N:25]1CCOCC1)C.C(OC(Cl)=O)C(C)C.N>O1CCCC1.C(OCC)(=O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:13]([NH2:25])=[O:14])[CH2:3][S:4][CH2:5][C:6]1[CH:12]=[CH:11][C:9]([CH3:10])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 6992557HCID 6992557, compound

Product 1

HCID 14390816HCID 14390816, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 g of BOC-D-Cys(MBzl)-OH are dissolved in 60 cc of dry tetrahydrofuran, the solution is cooled to -15°, 1.85 cc of N-ethylmorpholine are added, and then 1.92 cc of chloroformic acid isobutyl ester are added, and the mixture is stirred for 10 minutes. Dry ammonia gas is subsequently passed through the solution at -15° while stirring, stirring is continued for 2 hours, whereby the temperature rises to room temperature. The reaction mixture is diluted with approximately 800 cc of ethyl acetate, is washed with water, and the organic phase is dried over sodium sulphate. Concentration, filtration, washing with ethyl acetate/ether and drying are effected, and the title compound is obtained. M.P. 140°; [α]D20 = +26° in dimethyl formamide.

Workup

  1. temperaturethe solution is cooled to -15°
  2. customis subsequently passed through the solution at -15°
  3. stirringwhile stirring
  4. stirringstirring
  5. waitis continued for 2 hours
  6. customrises to room temperature
  7. washis washed with water
  8. dry with materialthe organic phase is dried over sodium sulphate
  9. concentrationConcentration, filtration
  10. washwashing with ethyl acetate/ether
  11. customdrying

Sources & evidence

ORD record
ord-8faf0279d34c4905bd2fecf203257a7b
Source dataset
uspto-grants-1978_10
Patent number
US04120852

Reaction notes

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