Ammonia → HCID 68439347, compound

HRID 276713Notes

Reaction equation

HRID 276713 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([NH:14][C:15](=[O:32])[CH:16]([NH:21]C(OCC1C=CC=CC=1)=O)[CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:34]1CCOCC1.[CH2:40]([O:44][C:45](Cl)=[O:46])[CH:41]([CH3:43])[CH3:42].N.O1C[CH2:52][CH2:51][CH2:50]1>C(OCC)(=O)C>[CH2:40]([O:44][C:45](=[O:46])[NH:21][CH:16]([C:15](=[O:32])[NH:14][CH:10]([C:11](=[O:13])[NH2:34])[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:17][CH:18]([CH3:19])[CH3:20])[C:41]1[CH:43]=[CH:52][CH:51]=[CH:50][CH:42]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 18316686HCID 18316686, compound

Product 1

HCID 68439347HCID 68439347, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 0.980 g of 3-benzyloxy-2-(2-benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionic acid and 0.25 ml of N-methylmorpholine in 12 ml of tetrahydrofuran 0.3 ml of isobutylchloroformate is added dropwise at −15° C. The reaction mixture is stirred at −15° C. for 10 minutes, then 4 ml of aqueous NH3 (25%) is added dropwise over a time period of 5 minutes. The reaction mixture is stirred for additional 15 minutes and diluted with ethyl acetate. Ethyl acetate is washed once with saturated NH4Cl-solution and once with H2O, then dried sodium sulfate, the solvent is removed und the residue is triturated with diethylether.

Workup

  1. stirringThe reaction mixture is stirred for additional 15 minutes
  2. washEthyl acetate is washed once with saturated NH4Cl-solution and once with H2O
  3. customdried sodium sulfate, the solvent is removed und the residue
  4. customis triturated with diethylether

Sources & evidence

ORD record
ord-34dadf3ead3148fc9b2a347ab8b7dd4a
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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