Acetyl chloride → HCID 69489035, compound

HRID 1531496Notes

Reaction equation

HRID 1531496 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][CH2:48][NH2:49])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:57](Cl)(=[O:59])[CH3:58]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][CH2:48][NH:49][C:57](=[O:59])[CH3:58])=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69486530HCID 69486530, compound

Product 1

HCID 69489035HCID 69489035, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 0.070 g (0.104 mmol) of (3R,4R)-3-[1-(3-amino-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester [example 10(c)] and 0.013 g (0.125 mmol, 1.2 equiv.) of triethylamine in 1 ml of dichloromethane was added dropwise 0.009 g (0.114 mmol, 1.1 eqiuv.) of acetyl chloride. The reaction was allowed to warm to room temperature, poured into 50 ml of an ice/water mixture and extracted three times with 50 ml of ethyl acetate. The combined organic phases were washed twice with 20 ml of water, evaporated under reduced pressure and dried in a high vacuum. The thus-obtained crude product was purified by chromatography on silica gel using ethyl acetate as the eluent and yielded 0.068 g (0.095 mmol, 91.3% of theory) of (3R,4R)-3-[1-(3-acetylamino-propyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester as a light yellow oil; MS: 716 (M+H)+.

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate
  2. washThe combined organic phases were washed twice with 20 ml of water
  3. customevaporated under reduced pressure
  4. customdried in a high vacuum
  5. customThe thus-obtained crude product
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1dba8a61e136406d8d620caff899917f
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

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