HCID 69286088, compound → HCID 86596954, compound

HRID 2225269Notes

Reaction equation

HRID 2225269 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][CH2:16][C:17]([NH:19][C@H:20]2[CH2:25][CH2:24][C@@H:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][C@H:21]2[C:33]([OH:35])=[O:34])=[O:18])=[O:14])=[CH:11][C:10]=1[C:38]([CH3:41])([CH3:40])[CH3:39])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:29]([O:28][C:26]([C@H:23]1[CH2:22][C@@H:21]([C:33]([OH:35])=[O:34])[C@@H:20]([NH:19][C:17](=[O:18])[CH2:16][NH:15][C:13](=[O:14])[C:12]2[CH:36]=[CH:37][C:9]([OH:8])=[C:10]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:11]=2)[CH2:25][CH2:24]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 69286088HCID 69286088, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86596954HCID 86596954, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of (1R,2S,5R)-2-(2-(4-(benzyloxy)-3-tert-butylbenzamido)acetamido)-5-(tert-butoxycarbonyl)cyclohexanecarboxylic acid (100 mg, 0.17 mmol) and 10% Pd/C (100 mg) in MeOH (10 mL) was exposed to an atmosphere of hydrogen for 14 h. The reaction mixture was filtered through diatomaceous earth, rinsed with MeOH (400 mL) and concentrated in vacuo to provide (1R,2S,5R)-5-(tert-butoxycarbonyl)-2-(2-(3-tert-butyl-4-hydroxybenzamido)acetamido)cyclohexanecarboxylic acid (87 mg, quant.) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.79-7.78 (m, 1H), 7.61-7.58 (m, 1H), 6.80-6.75 (m, 1H), 4.59 (s, 1H), 3.99 (s, 2H), 3.45-2.89 (m, 4H), 2.54 (s, 1H), 2.18-1.25 (m, 6H), 1.42 (s, 9H), 1.41 (s, 9H); MS found: (M+H)+=492.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washrinsed with MeOH (400 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29053c44137f4b328e832e7c6f66fe5f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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