HCID 117740009, compound → (S)-tert-butyl 1-((S)-2-amino-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)pyrrolidine-2-carboxylate

HRID 1775856Notes

Reaction equation

HRID 1775856 reaction equation
C(OC([NH:11][C@@H:12]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[CH:42][CH:41]=3)=[CH:36][N:35]=2)=[CH:30][CH:29]=1)[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:14])=O)C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[NH2:11][C@@H:12]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[CH:42][CH:41]=3)=[CH:36][N:35]=2)=[CH:30][CH:29]=1)[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:14]

Participants

5

Reactant 2

HCID 117740009HCID 117740009, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117741043(S)-tert-butyl 1-((S)-2-amino-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)pyrrolidine-2-carboxylateYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared using General Procedure 18: A solution of (S)-tert-butyl 1-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)pyrrolidine-2-carboxylate (436 mg, 0.6 mmol) in THF (25 mL) was hydrogenated in the H-Cube using a 10% Pd/C CatCart at 60° C. (Full hydrogen, 1 mL/min). The reaction mixture was passed over the catalyst a second time at 65° C. The solvent was removed to give 307 mg (83%) of (S)-tert-butyl 1-((S)-2-amino-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)pyrrolidine-2-carboxylate INT-26 as a white powder. LCMS-ESI (m/z) calculated for C35H46N4O4: 586.4. found 587.4 [M+H]+, tR=6.99 min (Method 10).

Workup

  1. customPrepared
  2. customat 60° C.
  3. customat 65° C
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-da522b8a1b0645e0bc293c018b06a609
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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