Acetyl chloride → HCID 42635718, compound

HRID 1674680Notes

Reaction equation

HRID 1674680 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(OC([N:12]1[CH2:17][C@H:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:24]=3[CH:34]=2)[C@@H:15]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][O:42][CH2:43][C@H:44]([O:46][CH2:47][CH3:48])[CH3:45])=[CH:37][CH:36]=2)[C@H:14]([CH2:49][OH:50])[CH2:13]1)=O)(C)(C)C.CCN(CC)CC>C(Cl)Cl>[CH2:47]([O:46][C@H:44]([CH3:45])[CH2:43][O:42][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([C@@H:15]2[C@@H:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:24]=4[CH:34]=3)[CH2:17][NH:12][CH2:13][C@H:14]2[CH2:49][O:50][C:1](=[O:3])[CH3:2])=[CH:36][CH:37]=1)[CH3:48]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 42609851HCID 42609851, compound

Product 1

HCID 42635718HCID 42635718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.89 mmol of acetyl chloride are added to a solution of 0.81 mmol of (3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-hydroxymethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 1a) and 0.97 mmol of Et3N in 7 ml of CH2Cl2 under argon at 0° C. After 1 h, the reaction mixture is diluted with CH2Cl2 and washed with successively with saturated aqueous NaHCO3 solution and brine. The combined aqueous phases are extracted with CH2Cl2—the combined organic layers are dried over Na2SO4 and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and is identified based on the Rf value.

Workup

  1. washwashed with successively with saturated aqueous NaHCO3 solution and brine
  2. extractionThe combined aqueous phases are extracted with CH2Cl2—the combined organic layers
  3. dry with materialare dried over Na2SO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b8a80b1888fd4b6994f013876a024ae9
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

Loading…