Water → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 1462121Notes

Reaction equation

HRID 1462121 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 residue which was treated with water to give white solids. The solids 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 residue which
  4. customto give white solids
  5. filtrationThe solids were collected by filtration
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-a77a1a7fd06c4280aa611359b593eb10
Source dataset
uspto-grants-1984_07
Patent number
US04458078

Reaction notes

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