1-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

HRID 1719450Notes

Reaction equation

HRID 1719450 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:4](N[C@@H](C(OC)=O)CCC(=O)O)=[O:5])[CH3:3].N(C(OCC1C=CC=CC=1)=O)[C@H](C(N[C@@H](C(OCC1C=CC=CC=1)=O)CC(O[N:37]1[C:42](=[O:43])[CH2:41][CH2:40][C:38]1=[O:39])C(=O)O)=O)C.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=[O:72])=CC=1>C(Cl)Cl>[NH:1]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@@H:2]([C:4]([O:5][N:37]1[C:42](=[O:43])[CH2:41][CH2:40][C:38]1=[O:39])=[O:72])[CH3:3]

Participants

5

Reactant 3

HCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazoleHCID 131713573Boc-L-Ala-D-Glu(OH)OMeHCID 131714323Z-L-Ala-D-Glu(gamma-OSu)OBzl

Product 1

HCID 11580086N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl esterYield 188.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of Boc-L-Ala-D-Glu(OH)OMe (1)(1.33 g), L-Lys(ε-Boc)-GlyOEt (2)(2.02 g) and 1-(4-chlorobenzenesulfonyloxy)-6-chlorobenzotriazole (1.38 g) in methylene chloride (50 ml) was added N-methylmorphorine (0.808 g) at 0° C. and the mixture was stirred for 30 minutes at the same temperature and for 2 days at room temperature. The reaction mixture was washed successively with 5% aqueous sodium bicarbonate, water, 5% hydrochloride acid and water, dried over magnesium sulfate and evaporated to give a crystalline mass, which was washed with ether to give Boc-L-Ala-γ-D-Glu(α-OMe)-L-Lys(ε-Boc)-GlyOEt (3)(1.96 g).

Workup

  1. additionwas added N-methylmorphorine (0.808 g) at 0° C.
  2. washThe reaction mixture was washed successively with 5% aqueous sodium bicarbonate, water, 5% hydrochloride acid and water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crystalline mass, which
  6. washwas washed with ether

Sources & evidence

ORD record
ord-0bf9bff0f16649da8710b15b1fe91762
Source dataset
uspto-grants-1985_09
Patent number
US04539155

Reaction notes

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