Acetic Anhydride → HCID 69147614, compound

HRID 2218265Notes

Reaction equation

HRID 2218265 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[C:20]([O:21][CH2:22][CH:23]([CH3:26])[CH2:24]C)=[CH:19][CH:18]=[CH:17][C:16]=2[O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:12]=[C:11]([C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[C:39]([OH:44])[CH:38]=2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(OCC)(=O)C>[C:45]([NH:43][C:40]1[CH:41]=[CH:42][C:37]([C:11]2[C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])=[C:2]([NH2:1])[N:14]=[C:13]([C:15]3[C:16]([O:27][CH2:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)=[CH:17][CH:18]=[CH:19][C:20]=3[O:21][CH2:22][CH:23]3[CH2:26][CH2:24]3)[CH:12]=2)=[CH:38][C:39]=1[OH:44])(=[O:47])[CH3:46]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69147205Tert-butyl 2-amino-4-(4-amino-3-hydroxyphenyl)-6-[2-[(4-methoxybenzyl)oxy]-6-(2-methylbutoxy)phenyl]nicotinate

Product 1

HCID 69147614HCID 69147614, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-amino-4-(4-amino-3-hydroxyphenyl)-6-[2-[(4-methoxybenzyl)oxy]-6-(2-methylbutoxy)phenyl]nicotinate (2.46 g, 4.21 mmol) was added acetic anhydride (0.44 mL, 4.63 mmol). The mixture was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to give tert-butyl 4-[4-(acetylamino)-3-hydroxyphenyl]-2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}nicotinate. (2.65 g, 100%); LC-MS (M/z=626, M+1)

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-894637fd5d87490dbffbfe5b8e081891
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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