HCID 131734753, compound → HCID 117740635, compound

HRID 1775882Notes

Reaction equation

HRID 1775882 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([NH:12][C@@H:13]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[N:48]=[CH:47][C:46]([C:49]4[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[CH:51][CH:50]=4)=[CH:45][N:44]=3)=[CH:39][CH:38]=2)[C:14]([NH:16][C@H:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:18][C:19]([O:21]CC2C=CC=CC=2)=[O:20])=[O:15])=[O:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:32]([O:31][C:29](=[O:30])[C@@H:17]([NH:16][C:14](=[O:15])[C@@H:13]([NH:12][C:10]([C:8]1[S:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)=[O:11])[CH2:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]2[N:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[CH:51][CH:50]=3)=[CH:45][N:44]=2)=[CH:41][CH:42]=1)[CH2:18][C:19]([OH:21])=[O:20])([CH3:33])([CH3:34])[CH3:35]

Participants

4

Reactant 1

HCID 131734753HCID 131734753, compound

Product 1

HCID 117740635HCID 117740635, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared using General Procedures 18: To 4-benzyl 1-(tert-butyl) ((S)-2-(5-(tert-butyl)thiophene-2-carboxamido)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)-L-aspartate INT-47 (345 mg, 0.4 mmol) in THF (5 mL) was added 10% Pd/C (60 mg). The reaction vessel was flushed with hydrogen gas and the reaction was stirred vigorously under hydrogen overnight at room temperature. The reaction mixture was filtered to remove the catalyst, the solvent was removed, and the crude product was purified by chromatography 0-100% EA in hexane to afford 228 mg (66%) of (S)-4-(tert-butoxy)-3-((S)-2-(5-(tert-butyl)thiophene-2-carboxamido)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanamido)-4-oxobutanoic acid INT-44 as a white solid. LCMS-ESI (m/z) calculated for C43H54N4O7S: 770.4. found 771.3 [M+H]+, tR=4.21 min (Method 16).

Workup

  1. customPrepared
  2. customThe reaction vessel was flushed with hydrogen gas
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. customthe solvent was removed
  6. customthe crude product was purified by chromatography 0-100% EA in hexane

Sources & evidence

ORD record
ord-990d7fd91c3f40b8859d1123a722b2e8
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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