HCID 117741085, compound → HCID 117740331, compound

HRID 1775890Notes

Reaction equation

HRID 1775890 reaction equation
C(OC([NH:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:38][CH:37]=3)=[CH:32][N:31]=2)=[CH:26][CH:25]=1)[C:13]([N:15]1[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]1)=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:35]=[CH:34][C:33]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:40][CH:41]=3)=[CH:32][N:31]=2)=[CH:26][CH:25]=1)[C:13]([N:15]1[CH2:16][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:18]1)=[O:14]

Participants

4

Reactant 1

HCID 117741085HCID 117741085, compound

Product 1

HCID 117740331HCID 117740331, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared using General Procedure 18: A solution of (S)-methyl 1-(2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)-propanoyl)azetidine-3-carboxylate (1.2 g, 1.81 mmol) in MeOH (150 mL) was passed over a 10% Pd/C CatCart (55×4 mm) at 65° C. in a Thales Nanotechnology H-Cube reactor at 2.1 mL/min. The solvent was evaporated and the residue purified by column chromatography (Ammonia/MeOH/DCM) to afford 604 mg (63%) of (S)-methyl 1-(2-amino-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)azetidine-3-carboxylate. LCMS-ESI (m/z) calculated for C31H38N4O4: 530.3. found 531.0 [M+H]+, tR=1.60 min (Method 6).

Workup

  1. customPrepared
  2. customThe solvent was evaporated
  3. customthe residue purified by column chromatography (Ammonia/MeOH/DCM)

Sources & evidence

ORD record
ord-f5d0d0655c9742c094cdbc034556ae77
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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