Acetic Anhydride → HCID 59478804, compound

HRID 1747095Notes

Reaction equation

HRID 1747095 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:18]([C:19]([NH:21][CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][OH:31])[N:25]=2)[CH3:23])=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:32])[N:10]1[C@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]1[NH:39][S:40]([CH3:43])(=[O:42])=[O:41].C(N(CC)CC)C.[C:51](OC(=O)C)(=[O:53])[CH3:52]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[C:51]([O:31][CH2:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH:22]([NH:21][C:19]([C@@H:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:32])[N:10]([C@H:33]3[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]3[NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[C@H:9]2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[O:20])[CH3:23])[N:25]=1)(=[O:53])[CH3:52]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59478260HCID 59478260, compound

Product 1

HCID 59478804HCID 59478804, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 714 mg of (3R,4R)-3-(2,4-dichlorophenyl)-N-{1-[6-(hydroxymethyl)pyridin-2-yl]ethyl}-2-{(1S,2S)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide in 14.3 ml of chloroform was cooled to 0° C., and 0.23 ml of triethylamine, 0.16 ml of acetic anhydride, and 6.8 mg of DMAP were added thereto in this order, followed by stirring at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, and ethyl acetate-water was added thereto for liquid separation, followed by washing with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain {6-[1-({[(3R,4R)-3-(2,4-dichlorophenyl)-2-{(1S,2S)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)ethyl]pyridin-2-yl}methyl acetate.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate-water
  2. additionwas added
  3. customfor liquid separation
  4. washby washing with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af8e43e6cf7b40348e785f93a799cf46
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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