1-Hydroxybenzotriazole → HCID 15601613, compound

HRID 652378Notes

Reaction equation

HRID 652378 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].S(O)(C1C=CC(C)=CC=1)(=O)=O.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 15601613HCID 15601613, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Phe-OH (79.6 g, 0.3 mole), Gly-OBzl-TosOH (111 g, 1.1 eq), and HOBt (44.6 g, 1.1 eq) were dissolved in DMF (300 ml). WSCI (60.4 ml, 1.1 eq ) was added dropwise while cooling, and the solution was stirred overnight. DMF was distilled off. The residue was dissolved in CHCl3, and the solution was washed with 5% NaHCO3, 10% Na2CO3, water, 1HCl, and water, in order, and dried over MgSO4. The CHCl3 was distilled off, and to the residue, Et2O was added. The thus-produced powder was obtained by filtration and recrystalized two times with AcOEt/Et2O to obtain the object product (59 g).

Workup

  1. additionWSCI (60.4 ml, 1.1 eq ) was added dropwise
  2. temperaturewhile cooling
  3. distillationDMF was distilled off
  4. dissolutionThe residue was dissolved in CHCl3
  5. washthe solution was washed with 5% NaHCO3, 10% Na2CO3, water
  6. dry with material1HCl, and water, in order, and dried over MgSO4
  7. distillationThe CHCl3 was distilled off
  8. additionto the residue, Et2O was added
  9. customThe thus-produced powder was obtained by filtration
  10. customrecrystalized two times with AcOEt/Et2O

Sources & evidence

ORD record
ord-a3aaa56cb23f457999e881dd38e142ef
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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