Water → HCID 69750535, compound

HRID 497472Notes

Reaction equation

HRID 497472 reaction equation
C[O:2][C:3]([C@H:5]1[C@H:10]([NH:11][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6]1)=[O:4].CC(C)([O-])C.[Na+].O>O1CCCC1.C(O)(C)(C)C>[C:23]([O:22][C:20]([N:7]1[CH2:8][CH2:9][C@@H:10]([NH:11][C@@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 66953071HCID 66953071, compound

Product 1

HCID 69750535HCID 69750535, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a dry flask (3R,4R)-4-[(R)-1-Phenyl-ethylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (4.50 g, 12.4 mmol) was dissolved in tetrahydrofuran (170 mL) and t-butanol (11 mL), and sodium t-butoxide (04.85 g, 50.5 mmol)was added. The reaction mixture was stirred for 16 hours. Water was added and the mixture was extracted with ethyl acetate five times. There was minimal residue after concentration in vacuo of the combined organic extracts. The aqueous extract was acidified to pH 3 with 1N hydrochloric acid, saturated with sodium chloride and then extracted five times with ethyl acetate. The combined organic layers were dried with magnesium sulfate, filtered and concentrated in vacuo to give an orange glass (2.11 g, 49%). MS (ESI), m+/z: (M+H)+=349.2.

Workup

  1. extractionthe mixture was extracted with ethyl acetate five times
  2. concentrationafter concentration in vacuo of the combined organic extracts
  3. extractionThe aqueous extract
  4. extractionextracted five times with ethyl acetate
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04f7e5ec7a4f4f6bbcfee4236c49af09
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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