Ammonia → HCID 11738220, compound

HRID 1789786Notes

Reaction equation

HRID 1789786 reaction equation
[Na].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH:16]([C:26]([OH:28])=[O:27])[CH2:17][S:18]CC2C=CC=CC=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].N.[Cl-].[NH4+]>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH:16]([C:26]([OH:28])=[O:27])[CH2:17][SH:18])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 54403892HCID 54403892, compound

Product 1

HCID 11738220HCID 11738220, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium metal (513 mg, 22.5 mmol) was added in portions during 5 min. to a solution of 4-(3-Benzylsulfanyl-2-carboxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.9 g, 2.29 mmol) in THF (45 mL) and liquid ammonia (50 mL) at −60° C. under argon. After stirring for 15 min. ammonium chloride (1.7 g, 31.5 mmol) was added in portions. The cooling bath was removed and the ammonia was evaporated using a stream of argon. 0.5 M NaOH was added and the mixture was washed with heptane. The aqueous phase was acidified with 2 M HCl and extracted with methylene chloride. The organic phase was washed with brine, dried and concentrated under reduced pressure to give 4-(2-Carboxy-3-mercapto-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.7 g, 100%).

Workup

  1. additionwas added in portions
  2. customThe cooling bath was removed
  3. customthe ammonia was evaporated
  4. addition0.5 M NaOH was added
  5. washthe mixture was washed with heptane
  6. extractionextracted with methylene chloride
  7. washThe organic phase was washed with brine
  8. customdried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-503d8f8f951340d2a25790799eb1eb45
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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