Hydrochloric Acid → HCID 18463947, compound

HRID 2231095Notes

Reaction equation

HRID 2231095 reaction equation
C([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH2:17][N:18]2[C:24](=[O:25])[CH:23]([NH:26][C:27](=[O:37])[C:28]3[CH:33]=[C:32]([Cl:34])[C:31]([OH:35])=[C:30]([Cl:36])[CH:29]=3)[CH2:22][CH2:21][CH2:20][N:19]2[S:38]([CH3:41])(=[O:40])=[O:39])=[O:16])[CH2:12][C:11](=[O:42])[O:10]1)C1C=CC=CC=1.Cl>CC#N>[Cl:36][C:30]1[CH:29]=[C:28]([CH:33]=[C:32]([Cl:34])[C:31]=1[OH:35])[C:27]([NH:26][CH:23]1[C:24](=[O:25])[N:18]([CH2:17][C:15]([NH:14][CH:13]([CH:9]=[O:8])[CH2:12][C:11]([OH:42])=[O:10])=[O:16])[N:19]([S:38]([CH3:41])(=[O:39])=[O:40])[CH2:20][CH2:21][CH2:22]1)=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18463948HCID 18463948, compound

Product 1

HCID 18463947HCID 18463947, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-{2-[(2-Benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-1-methanesulfonyl-3-oxo-[1,2]diazepan-4-yl}-3,5-dichloro-4-hydroxy-benzamide (26b) was stirred in CH3CN (0.5 mL) and 2N HCl (1 mL) for 7 hours. The solution was concentrated in vacuo to half of the volume and extracted with ether (2 mL×4). The combined ether layers was diluted with ethyl acetate/hexane (1/9, 3 mL), washed with 1M Na2CO3 (2 mL). The aqueous solution was washed with ethyl acetate/hexane (1/9, 2 mL×2), acidified with 6N HCl to pH˜3, extracted with ethyl acetate (1.5 mL×3). The combined extracts were dried over anhydrous Na2SO4, filtered and concentrated to dryness in vacuo to afford 20 mg (47% yield) of the title compound. 1H-NMR (500 MHz, CDCl3 +CD3OD) δ 0.75-0.90 (m, 1H), 1.18-1.30 (m, 3H), 1.67-1.88 (m, 1H), 1.93-2.30 (m, 2H), 2.40-2.61 (m, 1H), 3.10-3.16 (m, 3H), 3.95-4.30 (m, 2H), 4.30-4.50 (m, 1H), 5.00-5.08 (d, 1H), 7.81 (s, 2H). Analytical HPLC: 8.10 min. LC-MS (ES+): m/e=553, 555 (M+H+).

Workup

  1. concentrationThe solution was concentrated in vacuo to half of the volume
  2. extractionextracted with ether (2 mL×4)
  3. additionThe combined ether layers was diluted with ethyl acetate/hexane (1/9, 3 mL)
  4. washwashed with 1M Na2CO3 (2 mL)
  5. washThe aqueous solution was washed with ethyl acetate/hexane (1/9, 2 mL×2)
  6. extractionextracted with ethyl acetate (1.5 mL×3)
  7. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-65a7b02db685448184e71d945e1ef267
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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