Hydrochloric Acid → 1-Propenyl 3-O-benzyl-4-O-chloroacetyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

HRID 2413045Notes

Reaction equation

HRID 2413045 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([OH:19])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16][C@@H:11]([O:12][CH:13]=[CH:14][CH3:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:57][CH2:58][C:59](Cl)=[O:60].Cl>O.C(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]1[C@H:18]([O:19][C:59](=[O:60])[CH2:58][Cl:57])[C@@H:17]([CH2:20][O:21][C:22](=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:16][C@@H:11]([O:12][CH:13]=[CH:14][CH3:15])[C@@H:10]1[NH:39][C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 544293391-propenyl 3-O-benzyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Product 1

HCID 867398791-Propenyl 3-O-benzyl-4-O-chloroacetyl-2-deoxy-2-palmitamido-6-O-palmitoyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 0.4 g. of Compound 7 in 15 ml. of CH2Cl2 was added 0.4 ml. of pyridine. The reaction mixture was cooled to about 0° C. and 0.4 ml. chloroacetyl chloride in 5 ml. of CH2Cl2 was added dropwise with stirring. After stirring at room temperature for 30 minutes, thin layer chromatography showed the reaction was complete. Next water was added, then 5% HCl followed by a wash with water and NaHCO3. The dried chloroform layer was evaporated and the residue taken up in hot methanol and the solid material filtered off. Thin layer chromatography showed the solid material to be Compound 8 of high purity.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. washa wash with water and NaHCO3
  3. customThe dried chloroform layer was evaporated
  4. filtrationthe solid material filtered off

Sources & evidence

ORD record
ord-3298d7f762554ddfa02d474e737a5d26
Source dataset
uspto-grants-1985_01
Patent number
US04495346

Reaction notes

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