Water → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 2292176Notes

Reaction equation

HRID 2292176 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[C:35](Cl)(=[O:53])[CH2:36][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][CH3:52].O>C(Cl)Cl>[NH:1]([C:35]([CH2:36][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][CH3:52])=[O:53])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:11])[OH:12])=[O:5])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8212Stearoyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 12883963L-Ala-D-Glu(OH)OBzl

Product 1

HCID 131713574stearoyl-L-Ala-D-Glu(OH)OBzlYield 93.7%

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 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 residue 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-f8b00c2144a443138acbd37bb27f30e7
Source dataset
uspto-grants-1989_01
Patent number
US04801580

Reaction notes

Loading…