Acetic Anhydride → 5''-Acetylamino-2-benzyloxy-5-chloro[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

HRID 269528Notes

Reaction equation

HRID 269528 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[C:15]([C:20]2[C:21]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[C:17]([NH2:19])[CH:18]=1)=[O:12])[CH3:9]>N1C=CC=CC=1.C(OCC)C>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[C:15]([C:20]2[C:21]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[C:17]([NH:19][C:1](=[O:3])[CH3:2])[CH:18]=1)=[O:12])[CH3:9]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 587310045''-Amino-2-benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

Product 1

HCID 587309985''-Acetylamino-2-benzyloxy-5-chloro[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Acetic anhydride (53 mg, 0.5 mmol) was added to a solution of 5″-amino-2-benzyloxy-5-chloro-[1,1′;2′,1″]terphenyl-3″-carboxylic acid ethyl ester (96 mg, 0.21 mmol) in pyridine (2 ml) and the mixture left at room temperature for 1 hour. The resulting solution was diluted with diethyl ether, washed with 1M hydrochloric acid and saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to dryness to yield the title compound as a colourless gum. (102 mg, 97%).

Workup

  1. washwashed with 1M hydrochloric acid and saturated sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-acef4e26b0c04df7b2a8deb3140a092e
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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