Acetic Anhydride → HCID 57429031, compound

HRID 244795Notes

Reaction equation

HRID 244795 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:37])[CH2:16][N:17]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2([CH3:29])[CH2:26][C:25]3[C:20](=[CH:21][C:22]([CH3:28])=[C:23]([CH3:27])[CH:24]=3)[CH2:19]2)=[CH:11][C:10]=1[N+:38]([O-:40])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:37][C:41](=[O:43])[CH3:42])[CH2:16][N:17]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2([CH3:29])[CH2:26][C:25]3[C:20](=[CH:21][C:22]([CH3:28])=[C:23]([CH3:27])[CH:24]=3)[CH2:19]2)=[CH:11][C:10]=1[N+:38]([O-:40])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54392747HCID 54392747, compound

Product 1

HCID 57429031HCID 57429031, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[benzyl-(2,5,6-trimethyl-indan-2-yl)-amino]-ethanol in pyridine is added acetic anhydride and the mixture stirred for 18 hours. The reaction mixture is quenched with water and after addition of ethyl acetate washed twice with aqueous KHSO4 solution, twice with aqueous NaHCO3 and once with brine. The product is purified by chromatography (silica, ethyl acetate/hexane 1:4). ES+ MS m/e 579 (MH+)

Workup

  1. customThe reaction mixture is quenched with water
  2. additionafter addition of ethyl acetate
  3. washwashed twice with aqueous KHSO4 solution, twice with aqueous NaHCO3 and once with brine
  4. customThe product is purified by chromatography (silica, ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-c55d2a977d0b4e0cbbe372473269733e
Source dataset
uspto-grants-2014_02
Patent number
US08658673B2

Reaction notes

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