Acetic Anhydride → HCID 53476279, compound

HRID 1253571Notes

Reaction equation

HRID 1253571 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH:8]1([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[CH:28]=[C:29]([C:31]5[CH:36]=[CH:35][C:34]([CH2:37][NH:38][CH2:39][CH2:40][O:41][CH3:42])=[CH:33][N:32]=5)[S:30][C:23]=34)=[C:17]([F:43])[CH:16]=2)=[O:13])[CH2:10][CH2:9]1.CO.C(Cl)Cl>C(O)=O>[CH:8]1([NH:11][C:12](=[O:13])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[CH:28]=[C:29]([C:31]5[N:32]=[CH:33][C:34]([CH2:37][N:38]([CH2:39][CH2:40][O:41][CH3:42])[CH:1]=[O:3])=[CH:35][CH:36]=5)[S:30][C:23]=34)=[C:17]([F:43])[CH:16]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 21226129Dichloromethane methanolHCID 44229901HCID 44229901, compound

Product 1

HCID 53476279HCID 53476279, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To solution of acetic anhydride (150 μL, 1.17 mmol) in formic acid (2 mL) stirred at RT for 20 min was added in one portion 1 (150 mg, 0.296 mmol). After 2 hr, 200 μL of acetic anhydride (1.57 mmol) were added dropwise. The reaction mixture was stirred at RT overnight, quenched by addition of MeOH and concentrated. The residue was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV, then 10/90 over 5 CV), to afford the title compound 6 (96 mg, 0.18 mmol, 76% yield) as an off-white fluffy solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): mixture of rotamers, 8.75 (s, 1H), 8.60-8.50 (m, 2H), 8.37 and 8.34 (2s, 1H), 8.32-8.23 (m, 114), 8.15 (s, 1H), 7.90-7.77 (m, 1H), 7.73 (dd, J=13.5, 2.5 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.20 (bd, J=10.2 Hz, 1H), 6.67-6.58 (m, 2H), 4.60 and 4.56 (2s, 2H), 3.46-3.36 (m, 4H), 3.21 and 3.19 (2s, 3H), 2.59-2.51 (m, 1H), 0.70-0.60 (m, 2H), 0.47-0.38 (m, 2H). MS (m/z): 536.4 (M+H).

Workup

  1. customquenched by addition of MeOH
  2. concentrationconcentrated
  3. customThe residue was purified by Biotage (SNAP 25 g cartridge

Sources & evidence

ORD record
ord-77282e11d8d8442294230d232d4ef8f7
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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