BOC-D-alanine → Boc-(D)Ala-Gly-OBzl

HRID 652375Notes

Reaction equation

HRID 652375 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:33]([CH2:35][NH2:36])=[O:34])=[CH:27][CH:26]=1>C(Cl)Cl>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([NH:36][CH2:35][C:33]([O:32][CH2:31][C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)=[O:34])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 637606BOC-D-alanineHCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 15567200Boc-(D)Ala-Gly-OBzlYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-D-Ala-OH (5.68 g, 30 mmole) and H-Gly-OBzl.TosOH (10.6 g, 1.05 eq) were suspended in CH2Cl2. WSCI (6 ml, 1.1 eq) was added dropwise while cooling, and the solution was stirred overnight. The CH2Cl2 was distilled off. The residue was dissolved in AcOEt (500 ml); washed with 1N HCl, water, 5% NaHCO3, and water in order; and dried over Na2SO4. AcOEt was distilled off, and the residue was recrystalized twice with AcOEt/n-hexane to give the desired product (9.16 g, 90.7%).

Workup

  1. additionWSCI (6 ml, 1.1 eq) was added dropwise
  2. temperaturewhile cooling
  3. distillationThe CH2Cl2 was distilled off
  4. dissolutionThe residue was dissolved in AcOEt (500 ml)
  5. washwashed with 1N HCl, water, 5% NaHCO3, and water in order
  6. dry with materialand dried over Na2SO4
  7. distillationAcOEt was distilled off
  8. customthe residue was recrystalized twice with AcOEt/n-hexane

Sources & evidence

ORD record
ord-704b84efe0ee494a8263c3f78ceb2203
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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