Methanol → HCID 135410980, compound

HRID 601416Notes

Reaction equation

HRID 601416 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:17])[C:3]=1[C:18]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([NH:28][S:29]([NH:32][C:33]3[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=3)[C:36]([O:38]CC)=[O:37])(=[O:31])=[O:30])=[CH:27][C:21]=2[S:20](=[O:45])(=[O:44])[N:19]=1.CO>[OH-].[Na+]>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[C:4](=[O:17])[C:3]=1[C:18]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([NH:28][S:29]([NH:32][C:33]3[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=3)[C:36]([OH:38])=[O:37])(=[O:31])=[O:30])=[CH:27][C:21]=2[S:20](=[O:44])(=[O:45])[N:19]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 135410979HCID 135410979, compound

Product 1

HCID 135410980HCID 135410980, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of the product of Example 454 (25.5 mg, 0.389 mmol) in 1 mL of 1N aqueous sodium hydroxide and 1ML of methanol was stirred at 25° C. for 17 hours, and concentrated under a stream of warm nitrogen. The residue was treated with 2 mL of 1N aqueous hydrochloric acid. The resulting solid was isolated by vacuum filtration, washed with 10 mL of water, and dried to provide the title compound (21.4 mg, 88% yield). 1H NMR (300 MHz, DMSO-d6) δ 0.98 (d, J=6.62 Hz, 6 H) 1.56 (m, 2 H) 1.68 (m, 1 H) 4.48 (m, 2 H) 7.32-7.53 (m, 4 H) 7.59 (m, 2 H) 7.69 (d, J=8.82 Hz, 1 H) 7.75 (s, 1 H) 8.55 (dd, J=8.09, 1.84 Hz, 1 H) 8.88 (dd, J=4.78, 1.47 Hz, 1 H) 10.79 (s, 1 H) 10.88 (s, 1 H) 13.01 (bs, 1 H) 14.12 (bs, 1 H). MS (ESI+) m/z 627.1 (M+H)+, 649.1 (M+Na)+, (ESI−) m/z 625.1 (M−H)−.

Workup

  1. concentrationconcentrated under a stream of warm nitrogen
  2. additionThe residue was treated with 2 mL of 1N aqueous hydrochloric acid
  3. customThe resulting solid was isolated by vacuum filtration
  4. washwashed with 10 mL of water
  5. customdried

Sources & evidence

ORD record
ord-6f5e457521884f7493dd1d2bc8be8411
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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