Acetic Acid → HCID 71008487, compound

HRID 2273061Notes

Reaction equation

HRID 2273061 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][C@@H:15]([N:37]=[N+:38]=[N-:39])[CH2:16][CH2:17][C@H:18]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[O:7][C@H:6]1[N:40]1[CH:48]=[N:47][C:46]2[C:41]1=[N:42][C:43]([NH:50][CH2:51][CH2:52][NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[N:44][C:45]=2[NH2:49])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[NH2:49][C:45]1[N:44]=[C:43]([NH:50][CH2:51][CH2:52][NH:53][C:54]([O:56][C:57]([CH3:58])([CH3:59])[CH3:60])=[O:55])[N:42]=[C:41]2[C:46]=1[N:47]=[CH:48][N:40]2[C@@H:6]1[O:7][C@H:8]([CH2:14][C@@H:15]([N:37]=[N+:38]=[N-:39])[CH2:16][CH2:17][C@H:18]([NH:26][S:27]([C:30]2[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=2)(=[O:29])=[O:28])[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 86673682HCID 86673682, compound

Product 1

HCID 71008487HCID 71008487, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture consisting of Compound 28A in methanol is added potassium carbonate (10 molar equivalents) and the mixture stirred for 30 minutes at room temperature. Acetic acid is added to neutral pH and the solution is stirred 30 minutes. Solvent is evaporated and the mixture is partitioned between ethyl acetate and water. The organics are washed with brine, dried and evaporated. The residue is chromatographed on silica gel to obtain the title intermediate.

Workup

  1. stirringthe solution is stirred 30 minutes
  2. customSolvent is evaporated
  3. customthe mixture is partitioned between ethyl acetate and water
  4. washThe organics are washed with brine
  5. customdried
  6. customevaporated
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-111d344c9039454a9b8a6d795202dbd5
Source dataset
uspto-grants-2015_09
Patent number
US09120820B2

Reaction notes

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