N,N-Diethylethanamine trihydrofluoride → HCID 57978313, compound

HRID 1866496Notes

Reaction equation

HRID 1866496 reaction equation
[Si]([O:8][C@H:9]([C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([CH2:41][OH:42])[CH:35]=1)[CH2:10][NH:11][C:12]([CH3:33])([CH3:32])[CH2:13][C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][CH:31]=1)[C:17]([NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])=[O:18])(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C>>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][CH2:20][NH:19][C:17](=[O:18])[C:16]1[CH:29]=[CH:30][CH:31]=[C:14]([CH2:13][C:12]([NH:11][CH2:10][C@H:9]([OH:8])[C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([CH2:41][OH:42])[CH:35]=2)([CH3:33])[CH3:32])[CH:15]=1

Participants

3

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 69026019HCID 69026019, compound

Product 1

HCID 57978313HCID 57978313, compoundYield 77%

Procedure

A mixture of 3-[2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]-N-[2-(2-chlorophenyl)ethyl]benzamide (preparation 118), (147 mg, 0.24 mmol) and triethylamine trihydrofluoride (39 μL, 0.24 mmol) was stirred at room temperature for 3 days. The mixture was then concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 95:5:0.5. The appropriate fractions were evaporated under reduced pressure and the residue was azeotroped with methanolic ammonia to afford the title compound as a colourless solid in 77% yield, 75 mg. 1H NMR (400 MHz, CD3OD) δ: 7.61 (2H, m), 7.37-7.29 (5H, m), 7.23-7.16 (2H, m), 7.12 (1H, dd), 6.74 (1H, d), 4.66 (1H, m), 4.64 (2H, s), 3.63 (2H, m), 3.05 (2H, t), 2.96-2.84 (2H, t), 2.76-2.69 (2H, m), 1.10 (3H, s), 1.04 (3H, s) ppm; LRMS ESI m/z 497 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with dichloromethane
  4. customThe appropriate fractions were evaporated under reduced pressure
  5. customthe residue was azeotroped with methanolic ammonia

Sources & evidence

ORD record
ord-e013e782485c4c01b9d2658c29c2fe67
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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