Acetic Anhydride → HCID 135550584, compound

HRID 412297Notes

Reaction equation

HRID 412297 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH2:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=2[O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[N:3]=1.C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43]>O1CCCC1>[C:42]([NH:9][CH2:8][C:7]1[C:2]([NH2:1])=[N:3][C:4]([C:23]2[C:28]([OH:29])=[CH:27][CH:26]=[CH:25][C:24]=2[O:30][CH2:31][CH:32]2[CH2:33][CH2:34]2)=[CH:5][C:6]=1[CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 135550614HCID 135550614, compound

Product 1

HCID 135550584HCID 135550584, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of tert-butyl 3-{2-amino-3-(aminomethyl)-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-pyridinyl}-1-piperidinecarboxylate (1.9 g, 4.055 mmol) and triethylamine (1.13 mL, 8.109 mmol) in tetrahydrofuran (40.0 mL) was added acetic anhydride (0.457 mL, 4.865 mmol). The mixture was stirred at 0° C. for 4 hrs. After quenched by water, the mixture was extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue (yellow solid) was purified by recrystallization from ethyl acetate/diisopropyl ether to give tert-butyl 3-{3-(acetylamino-methyl)-2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-pyridinyl}-1-piperidinecarboxylate (1.13 g, yield; 55%).

Workup

  1. customAfter quenched by water
  2. extractionthe mixture was extracted with ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue (yellow solid) was purified by recrystallization from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-0cfd6139845e4a5297ab7763c31cb063
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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