Dimethylformamide → BOC-Thr(Bzl)-Pro-OBzl

HRID 435393Notes

Reaction equation

HRID 435393 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([OH:15])=O)[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.[NH:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36].Cl.CN(C=O)C>C1COCC1>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:13]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])=[O:15])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 1549483L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 15003996BOC-Thr(Bzl)-Pro-OBzlYield 108.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BOC-Thr(Bzl)-OH (32.88 g, 0.15 M) was dissolved in THF (100 ml). HOBT (20.94 g, 0.155 M) and H-Pro-OBzl.HCl (37.47 g, 0.155 M) were added thereto, and DMF (200 ml) was added to prepare a solution. WSCI (28.37 ml, 0.155 M) was added dropwise during 10 minutes while cooling with a freezing mixture, then the mixture was stirred at room temperature overnight. The solvent was distilled off in vacuo. Ethyl acetate (500 ml) was added to the residue, which was then washed with 5% aqueous sodium bicarbonate (twice), saturated sodium chloride solution, 1 N HCl (twice), saturated sodium chloride (twice) and water, in that order. After drying with anhydrous sodium sulfate, the solvent was distilled off and the mixture was concentrated in vacuo to obtain oil substance [5] (57.41 g, yield: 77.1%).

Workup

  1. customto prepare a solution
  2. additionWSCI (28.37 ml, 0.155 M) was added dropwise during 10 minutes
  3. temperaturewhile cooling with a freezing mixture
  4. distillationThe solvent was distilled off in vacuo
  5. additionEthyl acetate (500 ml) was added to the residue, which
  6. washwas then washed with 5% aqueous sodium bicarbonate (twice), saturated sodium chloride solution, 1 N HCl (twice), saturated sodium chloride (twice) and water
  7. dry with materialAfter drying with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off
  9. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ed3d209f96064f299fb2ef0e36304b83
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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