HCID 131734752, compound → HCID 117740494, compound

HRID 1775869Notes

Reaction equation

HRID 1775869 reaction equation
[C:1]([C:5]1[CH:63]=[CH:62][C:8]([C:9]([NH:11][C@@H:12]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[N:47]=[CH:46][C:45]([C:48]4[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[CH:50][CH:49]=4)=[CH:44][N:43]=3)=[CH:38][CH:37]=2)[C:13]([NH:15][C@H:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[C:31]([O:30][C:28](=[O:29])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:63][CH:62]=1)[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[N:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])=[CH:50][CH:49]=3)=[CH:44][N:43]=2)=[CH:40][CH:41]=1)[CH2:17][C:18]([OH:20])=[O:19])([CH3:32])([CH3:33])[CH3:34]

Participants

4

Reactant 1

HCID 131734752HCID 131734752, compound

Product 1

HCID 117740494HCID 117740494, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared using General Procedures 18: To 4-benzyl 1-(tert-butyl) ((S)-2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)-L-aspartate (50 mg, 0.058 mmol) in THF (2 mL) was added 10% Pd/C (10 mg). The reaction vessel was flushed with hydrogen gas and the reaction was stirred vigorously under hydrogen for 2 h at room temperature. The reaction mixture was filtered to remove the catalyst and the solvent was removed to give 38 mg (86%) of (S)-4-(tert-butoxy)-3-((S)-2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanamido)-4-oxobutanoic acid INT-31 as a white solid. LCMS-ESI (m/z) calculated for C45H56N4O7: 764.4. found 765.4 [M+H]+, tR=4.24 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

Sources & evidence

ORD record
ord-c2f0b6b12fd44657a562bb55f72850cc
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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