HCID 69654832, compound → HCID 69654950, compound

HRID 1061406Notes

Reaction equation

HRID 1061406 reaction equation
C([O:8][C:9](=[O:47])[CH2:10][N:11]([S:40]([CH2:43][CH2:44][CH2:45][CH3:46])(=[O:42])=[O:41])[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][CH2:25][C@H:26]([OH:39])[C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:28]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)C1C=CC=CC=1>[Pd].CO>[CH2:43]([S:40]([N:11]([CH2:10][C:9]([OH:47])=[O:8])[C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([NH:24][CH2:25][C@H:26]([OH:39])[C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:28]=3)[CH2:22][CH2:23]2)=[CH:16][CH:17]=1)(=[O:42])=[O:41])[CH2:44][CH2:45][CH3:46]

Participants

4

Reactant 1

HCID 69654832HCID 69654832, compound

Product 1

HCID 69654950HCID 69654950, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.18 g of [(butane-1-sulfonyl)-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidine-1-yl}-phenyl)-amino]-acetic acid benzyl ester (which was obtained in Example 342) and 0.05 g of 10% palladium on carbon in 15 mL of methanol was shaken on a Parr hydrogenator at 25 psi overnight. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo, which afforded a beige solid; 1H NMR (300 MHz, DMSO-d6) δ 0.86 (t, J=7.23 Hz, 3H), 1.29-1.41 (m, 2H), 1.48-1.51 (m, 2H), 1.54-1.73 (m, 2H), 1.92-2.09 (m, 2H), 2.57-2.64 (m, 2H), 2.79-2.87 (m, 2H), 2.94 (s, 3H), 3.00-3.07 (m, 4H), 3.16 (s, 2H), 3.20-3.26 (m, 2H), 3.64-3.75 (m, 2H), 4.02-4.04 (m, 2H), 4.77-4.81 (m,1H), 6.84-6.91 (m, 3H), 7.06 (dd, J=2.1 Hz, 8.4 Hz, 2H), 7.23 (d, J=1.8 Hz,1H), 7.34 (d, J=9.00 Hz, 2H); MS (ES) m/z: 599.0 (MH+); HRMS found for C26H38N4O8S2: 599.2202.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo, which
  3. customafforded a beige solid

Sources & evidence

ORD record
ord-89a0815dbf1d4c63a340332dc25d09e2
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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