Hydrochloric Acid → HCID 10099346, compound

HRID 863807Notes

Reaction equation

HRID 863807 reaction equation
CC(C)(OC([N:7]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[O:39][C:38]([CH2:40][CH2:41][CH:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[N:37][CH:36]=3)=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:21][CH:20]=1)[CH2:8][C@H:9]([OH:16])[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O)C.Cl>>[OH:16][C@H:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:8][NH:7][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[O:39][C:38]([CH2:40][CH2:41][CH:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[N:37][CH:36]=3)=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22866124HCID 22866124, compound

Product 1

HCID 10099346HCID 10099346, compoundYield 89.3%

Procedure

(R)-N-[4-[2-[N-(1,1-dimethylethoxycarbonyl)-N-[2-hydroxy-2-(pyridin-3-yl)ethyl]amino]ethyl]phenyl]-4-[2-(2-cyclopentylethyl)oxazol_ 5-yl]benzenesulfonamide (740 mg, 1.12 mmol) from Step D was treated with freshly prepared methanolic hydrogen chloride (5 mL) overnight. The solvent was removed under reduced pressure and the free base was isolated by column chromatography on silica gel (eluent: 1:9 10% ammonium hydroxide in methanol:methylene chloride) to afford the title compound as a white solid (560 mg, 89.3%): 1H NMR (500 MHz, CD3OD) δ8.52 (d, 1H, J=2.0 Hz), 8.43 (dd, 1H, J=1.5, 5 Hz), 7.81 (bd, H), 7.77 (d, 2H, J=8.5 Hz), 7.74 (d, 2H, J=8.5 Hz), 7.52 (s, 1H), 7.38 (dd, 1H, J=5, 7.5 Hz), 7.08 (d, 2H, J =8.5 Hz), 7.02 (d, 2H,J=8.5 Hz), 4.80 (m, 1H), 2.94-2.70 (m, 8H), 1.79 (m, 5H), 1.62 (m, 2H), 1.54 (m, 2H), 1.12 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe free base was isolated by column chromatography on silica gel (eluent: 1:9 10% ammonium hydroxide in methanol:methylene chloride)

Sources & evidence

ORD record
ord-0ad14fbb2d424489bdc8c97ac692cf75
Source dataset
uspto-grants-1996_10
Patent number
US05561142

Reaction notes

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