HCID 86705873, compound → HCID 72705162, compound

HRID 339240Notes

Reaction equation

HRID 339240 reaction equation
C(OC([N:8]([CH3:75])[C@@H:9]([CH3:74])[C:10]([NH:12][C@@H:13]([C:70]([CH3:73])([CH3:72])[CH3:71])[C:14]([N:16]1[C@H:25]([C:26](=[O:38])[NH:27][C@H:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][CH2:29]2)[CH2:24][C:23]2[C:18](=[CH:19][C:20]([C:39]([NH:41][C@@H:42]3[CH2:46][N:45]([C:47](OCC4C=CC=CC=4)=[O:48])[C@H:44]([C:57](=[O:69])[NH:58][C@H:59]4[C:68]5[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=5)[CH2:62][CH2:61][CH2:60]4)[CH2:43]3)=[O:40])=[CH:21][CH:22]=2)[CH2:17]1)=[O:15])=[O:11])=O)(C)(C)C>CO.[OH-].[OH-].[Pd+2]>[CH3:71][C:70]([CH3:73])([CH3:72])[C@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][CH3:75])[CH3:74])[C:14]([N:16]1[C@H:25]([C:26]([NH:27][C@H:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30][CH2:29]2)=[O:38])[CH2:24][C:23]2[C:18](=[CH:19][C:20]([C:39]([NH:41][C@H:42]3[CH2:43][C@@H:44]([C:57](=[O:69])[NH:58][C@H:59]4[C:68]5[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=5)[CH2:62][CH2:61][CH2:60]4)[N:45]([C:47](=[O:48])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][CH3:75])[CH3:74])[C:70]([CH3:71])([CH3:73])[CH3:72])[CH2:46]3)=[O:40])=[CH:21][CH:22]=2)[CH2:17]1)=[O:15]

Participants

4

Reactant 1

HCID 86705873HCID 86705873, compound

Product 1

HCID 72705162HCID 72705162, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 50 mL pressure flask containing Pd(OH)2 on carbon (2 mg, 0.02 mmol) was added a solution of (2S,4S)-benzyl 4-((S)-2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamido)-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate (177 mg, 0.17 mmol) in MeOH (5.8 mL). The resulting reaction mixture was stirred under H2 at 15 psi for 2 h and then filtered through a pad of CELITE® washing with EtOAc. The filtrate was concentrated in vacuo, and the resulting crude oil was purified using flash column chromatography (gradient elution from 0 to 10% NH3/MeOH/CH2Cl2) to give the title compound (80 mg, 52%) as a colorless oil. MS (ESI+) m/z 890.6 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a pad of CELITE®
  3. washwashing with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting crude oil was purified
  6. washflash column chromatography (gradient elution from 0 to 10% NH3/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6a9d2798bedf49fa97a51903d2adaf40
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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