Diethyl Ether → HCID 88182850, compound

HRID 2300962Notes

Reaction equation

HRID 2300962 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:18]2[CH:9]1[C:10]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:11]1[C:16]([CH2:17]2)=[CH:15][CH:14]=[C:13]([O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:31]1C=CC=C1CC(O)=O.[CH3:40][CH2:41][O:42]CC>>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:10]([CH2:29][CH3:30])([CH2:27][CH3:28])[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:19][C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH:12]=2)[CH2:17][C@H:18]1[S:31][C:41](=[O:42])[CH3:40])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 159702-Thiopheneacetic acidHCID 15923077HCID 15923077, compound

Product 1

HCID 88182850HCID 88182850, compound

Procedure

5-tert-Butoxycarbonyloxy-7,7-diethyl-1a,2,7,7a-tetrahydro-1-aza-cyclopropa[b]naphthalene-1-carboxylic acid tert-butyl ester (218 mg, 0.52 mmol) and the thiolacetic acid (2 mL) was stirred at r.t for over night. The mixture was diluted with Et2O (50 mL), washed with H2O, NaHCO3 (3×), H2O, brine, dried over MgSO4. The residu was purified by a flash chromatrgraphy (10% AcOEt/Hex) (234 mg, 91%). 1H NMR (CDCl3): 7.05-6.95 (3H, m, Har), 4.80 (1H, d, J=10.5 Hz, NH), 4.15-4.00 (2H, m, CHCH), 3.17 (1H, dd J=5 Hz and 17 Hz, PhCHH), 2.97 (1H, dd, J=12 Hz and 17 Hz, PhCHH), 2.40 (3H, s, SCOCH3), 1.86 (1H, m), 1.70 (2H, m), 1.60-1.55 (11H, m), 1.47 (9H, s, t-butyl), 0.89 (3H, t, J=7.5 Hz, CH3), 0.71 (3H, t, J=7.5 Hz, CH3).

Workup

  1. washwashed with H2O, NaHCO3 (3×), H2O, brine
  2. dry with materialdried over MgSO4
  3. customThe residu was purified by a flash chromatrgraphy (10% AcOEt/Hex) (234 mg, 91%)

Sources & evidence

ORD record
ord-dcbec7e968044d64898af60cdab553b1
Source dataset
uspto-grants-2002_12
Patent number
US06498196B1

Reaction notes

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