HCID 56630789, compound → HCID 10633927, compound

HRID 1532948Notes

Reaction equation

HRID 1532948 reaction equation
C(OC([NH:11][C@H:12]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]1=[O:27])=O)C1C=CC=CC=1>C(O)C>[NH2:11][C@H:12]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:13]1=[O:27]

Participants

3

Reactant 1

HCID 56630789HCID 56630789, compound

Product 1

HCID 10633927HCID 10633927, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl (3S)-3-benzyloxycarbonylamino-2-oxoperhydroazepine-1-acetate (15 g) was disolved in ethanol (150 ml) and purged with argon. 10% palladium or carbon (1.5 g) was added and the flask evacuated and filled with hydrogen from a balloon. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was then purged with argon and filtered through diatomaceous earth. The filtrate was evaporated to give tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate (7.7 g) as a viscous oil; NMR (CDCl3): 1.45 (s, 9H), 1.55-2.05 (m, 6H), 3.2-3.3 (d, 1H), 3.55-3.75 (two overlapping doublets, 2H), 3.95-4.25 (q, 2H); mass spectroscopy, m/e (ES+) 243.2 (MH+).

Workup

  1. custompurged with argon
  2. addition10% palladium or carbon (1.5 g) was added
  3. customthe flask evacuated
  4. additionfilled with hydrogen from a balloon
  5. customThe reaction mixture was then purged with argon
  6. filtrationfiltered through diatomaceous earth
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9a5742a42f7444b59c0104e5755b964f
Source dataset
uspto-grants-2001_03
Patent number
US06207644B1

Reaction notes

Loading…