Lithium hydroxide, monohydrate → HCID 67507069, compound

HRID 1791959Notes

Reaction equation

HRID 1791959 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][C:25]([C:28]([O:30]CC)=[O:29])=[CH:24][C:22]=4[N:23]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:33]([N:35]1[CH2:39][CH2:38][S:37][CH2:36]1)=[O:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(C1C=CC2OC(C3CCN([C@@H]4CN[C@H](C(N5CCSC5)=O)C4)CC3)=NC=2C=1)=O)C.O.[OH-].[Li+]>C(O)C.O.Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:22]=4[N:23]=3)[CH2:17][CH2:18]2)[CH2:10][C@H:9]1[C:33]([N:35]1[CH2:39][CH2:38][S:37][CH2:36]1)=[O:34])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21029498HCID 21029498, compoundHCID 67507415HCID 67507415, compound

Product 1

HCID 67507069HCID 67507069, compoundYield 80.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(5-ethoxycarbonyl-2 -benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 309 (3), 4.51 g] was dissolved in ethanol (16 mL) and water (8 mL), and lithium hydroxide monohydrate (678 mg) was added. The mixture was stirred at room temperature for 3.5 hr. The reaction mixture was diluted with water, and 1 mol/L hydrochloric acid was added to adjust its pH to 7. The mixture was extracted with chloroform. The extract was dried and concentrated under reduced pressure to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(5-carboxy-2-benzoxazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (3.45 g) as a white powder.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with chloroform
  3. customThe extract was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-139a19a6f6bb445a83961b53fe14abaf
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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