Water → HCID 67270758, compound

HRID 602488Notes

Reaction equation

HRID 602488 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH:20]([CH3:22])[CH3:21])[N:12]=2)=[O:10])[CH2:5][N:4]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].O>ClCCl>[C:37]([NH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH:20]([CH3:21])[CH3:22])[N:12]=2)=[O:10])[CH2:5][N:4]1[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67270764HCID 67270764, compound

Product 1

HCID 67270758HCID 67270758, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of tert-butyl (2S,4S)-2-(aminomethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate (202 mg, 0.5 mmol, step 2 of Example 17) and triethylamine (140 μL, 1.0 mmol) in dichloromethane (2 mL) was added acetyl chloride (43 μL, 0.55 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 h. The resulting solution was added to water and extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was PTLC eluting with dichloromethane/methanol (30:1 and 20:1 twice) to give 200 mg (90%) of the title compound as a colorless amorphous.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. washeluting with dichloromethane/methanol (30:1 and 20:1 twice)

Sources & evidence

ORD record
ord-3b4712351c504d02818de0b93da1954f
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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