Acetic Acid → HCID 89656185, compound

HRID 930957Notes

Reaction equation

HRID 930957 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([N:15]3[CH2:20][CH2:19][CH:18]([O:21]C4CCCCO4)[CH2:17][CH2:16]3)(=[O:14])=[O:13])=[CH:8][C:7]=2[C:28]2[C:29]3[CH:38]=[CH:37][NH:36][C:30]=3[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=2)[CH2:3][CH2:2]1.C(O)(=O)C.O1CCCC1>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([N:15]3[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]3)(=[O:13])=[O:14])=[CH:8][C:7]=2[C:28]2[C:29]3[CH:38]=[CH:37][NH:36][C:30]=3[C:31](=[O:35])[N:32]([CH3:34])[CH:33]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 89657622HCID 89657622, compound

Product 1

HCID 89656185HCID 89656185, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Example 354e (54 mg, 0.10 mmol), acetic acid (4 mL, 69.9 mmol), tetrahydrofuran (2 mL) and water (1 mL) was stirred at 45° C. for 2.5 hours. The reaction mixture was concentrated to dryness and the residue was dried overnight (in-vacuo). The crude product was triturated with diethyl ether, filtered and dried (in-vacuo) to afford the title compound (30 mg, 66% yield). 1H NMR (300 MHz, DMSO-d6) ppm 0.25-0.31 (m, 2H) 0.44-0.51 (m, 2H) 1.08-1.17 (m, 1H) 1.38-1.51 (m, 2H) 1.70-1.80 (m, 2H) 2.70-2.80 (m, 2H) 3.10-3.18 (m, 2H) 3.51-3.56 (m, 1H) 3.57 (s, 3H) 3.97 (d, J=6.78 Hz, 2H) 4.66 (d, J=4.07 Hz, 1H) 6.12 (t, J=2.71, 2.03 Hz, 1H) 7.27-7.32 (m, 2H) 7.36 (s, 1H) 7.64-7.70 (m, 2H) 12.04 (brs, 1H). MS (ESI+) m/z 458 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was dried overnight (in-vacuo)
  3. customThe crude product was triturated with diethyl ether
  4. filtrationfiltered
  5. customdried (in-vacuo)

Sources & evidence

ORD record
ord-f6afc27467314abdaf80ca7385c6139d
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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