Phthalimide → HCID 59512266, compound

HRID 1158489Notes

Reaction equation

HRID 1158489 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([CH2:25][N:26]([CH:42]([CH3:44])[CH3:43])[C:27](=[O:41])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:29]=2)[C@H:22]([CH2:45]O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[C:13]([O:17][C:18]([N:20]1[CH2:24][C@@H:23]([CH2:25][N:26]([CH:42]([CH3:44])[CH3:43])[C:27](=[O:41])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:29]=2)[C@H:22]([CH2:45][N:51]2[C:47](=[O:57])[C:48]3[C:49](=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:50]2=[O:52])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59512497HCID 59512497, compound

Product 1

HCID 59512266HCID 59512266, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

DEAD is slowly added to a solution of (3S,4R)-3-hydroxymethyl-4-({isopropyl-[3-(3-methoxy-propoxy)-4-methyl-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (210 mg, 0.44 mmol), phthalimide (07 mg, 0.66 mmol) and PPh3 (173 mg, 0.66 mmol) in THF (5 mL) at RT. The resulting yellow solution is stirred for another 2 h before H2O is added and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the extracts, filtration and evaporation of the solvent affords the crude product which is purified by preparative HPLC (Waters C18 ODB, eluent: CH3CN/H2O 5%/2 min, CH3CN/H2O 5-100%/10 min, 100% CH3CN/2.5 min, flow 20 mL/min) to give the desired product. MS (LC-MS): 630.2 [M+Na]+; tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 4.40 min.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. customDrying
  4. filtration(Na2SO4) of the extracts, filtration and evaporation of the solvent
  5. customaffords the crude product which
  6. customis purified by preparative HPLC (Waters C18 ODB, eluent: CH3CN/H2O 5%/2 min, CH3CN/H2O 5-100%/10 min, 100% CH3CN/2.5 min, flow 20 mL/min)

Sources & evidence

ORD record
ord-a51da07590364a2c84a354c2e9023f3a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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