Water → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 4421Notes

Reaction equation

HRID 4421 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[Si]([CH:28]([Si](C)(C)C)[C:29](N)=O)(C)C.C(Cl)(=O)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53].O>C(Cl)Cl>[NH:1]([C:17]([CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH3:37])=[O:19])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:29]1[CH:28]=[CH:9][CH:8]=[CH:7][CH:13]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8212Stearoyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 131713573Boc-L-Ala-D-Glu(OH)OMe

Product 1

HCID 131713574stearoyl-L-Ala-D-Glu(OH)OBzlYield 196.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Ala-D-Glu(OH)OBzl (1) (942 mg) was suspended in methylene chloride (40 ml), and bis(trimethylsilyl)acetamide (1.20 g) was added to the suspension under stirring. The resulting solution was treated with stearoyl chloride (900 mg) at ambient temperature and left for an hour. Evaporation of the solvent gave an oily residual which was treated with water to give white solides. The solides were collected by filtration, washed with water and dried over magnesium sulfate to give stearoyl-L-Ala-D-Glu(OH)OBzl (2) (1.60 g).

Workup

  1. waitleft for an hour
  2. customEvaporation of the solvent
  3. customgave an oily residual which
  4. customto give white solides
  5. filtrationThe solides were collected by filtration
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-9c82aae6872744659c78caf24f2a0ad6
Source dataset
uspto-grants-1988_02
Patent number
US04725582

Reaction notes

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