2,3-Dihydroxybutanedioic Acid → HCID 89499041, compound

HRID 1852356Notes

Reaction equation

HRID 1852356 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([NH:13][CH:14]([CH2:27][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C@@H:15]([C:17]1[CH:26]=[CH:25][C:20]2[O:21][CH2:22][CH2:23][O:24][C:19]=2[CH:18]=1)[OH:16])=[O:12].[C:33]([OH:42])(=[O:41])[CH:34]([CH:36]([C:38]([OH:40])=[O:39])[OH:37])[OH:35]>C(O)(C)C.CO>[C:38]([CH:36]([CH:34]([C:33]([OH:42])=[O:41])[OH:35])[OH:37])([OH:40])=[O:39].[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([NH:13][C@H:14]([CH2:27][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C@@H:15]([C:17]1[CH:26]=[CH:25][C:20]2[O:21][CH2:22][CH2:23][O:24][C:19]=2[CH:18]=1)[OH:16])=[O:12]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 89498906HCID 89498906, compound2×

Product 1

HCID 89499041HCID 89499041, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 2-(2,3-dihydro-1H-inden-2-yl)-N-((1R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)acetamide (compound 3h) (0.15 g, 0.34 mmol) in isopropanol (10 ml) was added a solution of (+)-tartaric acid (0.05 g, 0.34 mmol) in MeOH (5 mL). The resulting mixture was stirred 30 minutes, then concentrated in vacuo. EtOAc was added followed by diethyl ether (excess). The resulting solid was stirred 30 minutes, then allowed to set overnight. The solid was filtered, washed with diethyl ether, and dried overnight under high vacuum to yield 2-(2,3-dihydro-1H-inden-2-yl)-N-((1R,2R)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)acetamide tartrate, 0.16 g, 79% desired white solid. ESI-MS m/z 437.2 (M+H+). mp=174-175° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEtOAc was added
  3. stirringThe resulting solid was stirred 30 minutes
  4. waitto set overnight
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether
  7. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-65a934a70a844c90aff9a70cfa5ea941
Source dataset
uspto-grants-2015_02
Patent number
US08961959B2

Reaction notes

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