Benzyl chloroformate → HCID 67025956, compound

HRID 655933Notes

Reaction equation

HRID 655933 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]([NH2:13])=[O:12])[C:8]2[C:4](=[CH:5][N:6]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[N:7]=2)[CH:3]=1.[BH4-].[Na+].[CH:28]1[CH:33]=[CH:32][C:31]([CH2:34][O:35][C:36](Cl)=[O:37])=[CH:30][CH:29]=1>CO>[NH2:13][C:11]([C:9]1[C:8]2[C:4](=[CH:5][N:6]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]4[CH2:25][CH2:24][CH2:23][N:22]([C:36]([O:35][CH2:34][C:31]5[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=5)=[O:37])[CH2:21]4)=[CH:18][CH:19]=3)[N:7]=2)[CH:3]=[C:2]([F:1])[CH:10]=1)=[O:12]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 4311764Sodium borohydrideHCID 57502604HCID 57502604, compound

Product 1

HCID 67025956HCID 67025956, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (D4) in dry MeOH (0.2 M), NaBH4 (1.2 eq) was added and then dropwise Cbz-Cl (1.2 eq) at −65° C. The reaction was allowed to reach RT O/N, and then quenched with H2O. MeOH was concentrated under reduced pressure and EtOAc was added. The organic phase was washed with sat. aq. NaHCO3 solution, dried (Na2SO4). Evaporation of the solvent gave (D5) which was used in the next step without further purification. MS (ES) C27H25FN4O3 requires: 472. Found: 473 (M+H+).

Workup

  1. customat −65° C
  2. customto reach RT
  3. customquenched with H2O
  4. concentrationMeOH was concentrated under reduced pressure and EtOAc
  5. additionwas added
  6. washThe organic phase was washed with sat. aq. NaHCO3 solution
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e2253dface4541efb430cec802faaddc
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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