Acetic Acid → HCID 117598871, compound

HRID 522393Notes

Reaction equation

HRID 522393 reaction equation
[C:1]([C@H:5]1[C:41](=[O:42])[N:40]2[CH2:43][C@@H:37]([CH2:38][C@H:39]2[C:44]([O:46]C)=[O:45])[O:36][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:48][CH2:49][CH2:50][C@H:9]2[O:8][C:7](=[O:51])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].C(O)(=O)C>C1COCC1.C(O)C.C(OCC)(=O)C.O>[C:1]([C@H:5]1[C:41](=[O:42])[N:40]2[CH2:43][C@@H:37]([CH2:38][C@H:39]2[C:44]([OH:46])=[O:45])[O:36][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:48][CH2:49][CH2:50][C@H:9]2[O:8][C:7](=[O:51])[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 89590854HCID 89590854, compound

Product 1

HCID 117598871HCID 117598871, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the ester from Step 2 (55.8 mg) in THF (0.8 mL) and ethanol (0.2 mL) was added 2M LiOH (0.4 mL). After 1 hour at room temperature, the reaction was done. The mixture was diluted with ethyl acetate and water. Then, acetic acid was added until pH=5. The mixture was extracted with ethyl acetate (3×). The combined organics were dried over sodium sulfate, filtered and concentrated. LRMS (ES−) m/z 691.3 (M−H)−.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-11afab9a5c31431d9f7efd8d69086c79
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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