Water → HCID 68616453, compound

HRID 1158363Notes

Reaction equation

HRID 1158363 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([CH2:27][N:28]([CH:45]([CH3:47])[CH3:46])[C:29](=[O:44])[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH:31]=2)[C@H:24]([CH2:48][N:49]([C:53](=[O:62])[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([NH2:61])[CH:56]=2)[CH:50]2[CH2:52][CH2:51]2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>CN(C1C=CN=CC=1)C.C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([CH2:27][N:28]([CH:45]([CH3:47])[CH3:46])[C:29](=[O:44])[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH:31]=2)[C@H:24]([CH2:48][N:49]([C:53](=[O:62])[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([NH:61][C:8](=[O:10])[CH3:9])[CH:56]=2)[CH:50]2[CH2:51][CH2:52]2)[CH2:23]1)=[O:21])([CH3:17])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68617160HCID 68617160, compound

Product 1

HCID 68616453HCID 68616453, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (67 μL, 0.48 mmol), DMAP (0.4 mg, 0.003 mmol) and acetic anhydride (46 μL, 0.48 mmol) are added to a solution of (3R*,4R*)-3-({[2-(3-amino-phenyl)-acetyl]-cyclopropyl-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (215 mg, 0.32 mmol) in THF (20 mL). The reaction mixture is stirred at RT for 16 h before water is added for workup. Extraction with ethyl acetate, drying of the combined extracts (Na2SO4), filtration and evaporation of the solvent affords the crude product which is purified by flash chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 9:1) to give the title compound. MS (LC-MS): 709.1 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 6.04 min.

Workup

  1. additionis added for workup
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying of the combined extracts (Na2SO4), filtration and evaporation of the solvent
  4. customaffords the crude product which
  5. customis purified by flash chromatography on silica gel (eluent: CH2Cl2 to CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-7f4f9b2f07a545f8a2ad2b3c7c8ff042
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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