Benzylamine → HCID 23586350, compound

HRID 488903Notes

Reaction equation

HRID 488903 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH:12]([OH:22])[C:13](=[O:21])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N)C1C=CC=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH:12]([C:13](=[O:21])[NH:14][CH2:15][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:24]=1)[OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 69732763HCID 69732763, compound

Product 1

HCID 23586350HCID 23586350, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (2-hydroxy-2-phenylcarbamoyl-ethyl)-carbamic acid benzyl ester (250 mg, 1.045 mmol) was dissolved into 2 mL of dry DMF. To this was added PyBOP (652.3 mg, 1.254 mmol), HOBT (169.4 mg, 1.254 mmol), benzylamine (0.228 mL, 2.090 mmol) and DIPEA (0.728 mL, 4.18 mmol). The reaction stirred for 1.5 h. LC-MS analysis of the crude indicated complete consumption of the S.M. and the presence of the product. 40 mL of EtOAc was added and the organic mixture washed with 2×20 mL NH4Cl, 2×20 mL of H2O and 1×20 mL of brine. Dried organic phase with MgSO4, filtered and concentrated to a yellow film. Dissolved in CH2Cl2, applied to a SiO2 Column and purified (10-30% EtOAc/hexanes) to give a quantitative yield of (2-benzylcarbamoyl-2-hydroxy-ethyl)-carbamic acid benzyl ester.

Workup

  1. customconsumption of the S.M
  2. addition40 mL of EtOAc was added
  3. washthe organic mixture washed with 2×20 mL NH4Cl, 2×20 mL of H2O and 1×20 mL of brine
  4. filtrationDried organic phase with MgSO4, filtered
  5. concentrationconcentrated to a yellow film
  6. dissolutionDissolved in CH2Cl2
  7. custompurified (10-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5df15e0571784c75b687e73d459cbced
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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