Acetone → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 4422Notes

Reaction equation

HRID 4422 reaction equation
[NH:1]([C:17]([O:19]C(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].C(N([CH2:29][CH3:30])CC)C.C(OC(ON=[C:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:44]#N)=O)C1C=CC=CC=1.C(O[CH2:56][CH3:57])(=O)C.[CH3:58][C:59]([CH3:61])=O>O>[NH:1]([C:17]([CH2:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:46][CH2:43][CH2:44][CH2:56][CH2:57][CH2:29][CH3:30])=[O:19])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:59]1[CH:61]=[CH:4][CH:2]=[CH:3][CH:58]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3]

Participants

7

Reactant 5

HCID 180Acetone2×HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 540061222-Benzyloxycarbonyloxyimino-2-phenylacetonitrileHCID 131713573Boc-L-Ala-D-Glu(OH)OMe

Product 1

HCID 131713574stearoyl-L-Ala-D-Glu(OH)OBzlYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-mesoDAP-(L)-GlyOH (1) (1.2 g) in water (5 ml) was added triethylamine (0.96 g) and a solution of benzyloxycarbonyloxyimino-2-phenylacetonitrile (0.69 g) in acetone (5 ml) at 0° C. with stirring and the mixture was stirring over night at room temperature. After evapolation of acetone to the residue was added water (5 ml) and ethyl acetate (5 ml). The aqueous layer was separated, washed with ethyl acetate (5 ml), acidified with 1N-hydrochloric acid, and extracted with ethyl acetate (20 ml). The extract was washed with water (5 ml×2) and dried over magnesium sulfate. Evaporation of the solvent gave 1.42 g (94.7%) of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-Z-(D)-mesoDAP-(L)-GlyOH (2). ##STR551##

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate (5 ml)
  3. extractionextracted with ethyl acetate (20 ml)
  4. washThe extract was washed with water (5 ml×2)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cb80480d56a947c299041233295b2f80
Source dataset
uspto-grants-1988_02
Patent number
US04725582

Reaction notes

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