Benzoyl chloride → HCID 118353918, compound

HRID 525299Notes

Reaction equation

HRID 525299 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([C@H:9]([C:11](=[O:30])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C@H:20]1[CH2:28][NH2:29])=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[N:7]([C@H:9]([C:11](=[O:30])[NH:12][C@H:13]([C:17]([N:19]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH2:21][C@H:20]1[CH2:28][NH:29][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 118354449HCID 118354449, compound2×

Product 1

HCID 118353918HCID 118353918, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-1-[(S)-1-((S)-2-aminomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (intermediate 3) (100 mg 0.23 mmol) in DCM (4 mL) was cooled to 0-5° C. and triethylamine (0.08 mL 0.57 mmol) followed by benzoyl chloride (0.027 mL, 0.23 mmol) were added. The reaction was stirred at rt for 4 h. The reaction mixture was partitioned between water and DCM and the organic layer was then washed with water (30 mL×2) and brine (30 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by preparative-HPLC (acetonitrile and NH4OAc] to give ((S)-1-{(S)-1-[(S)-2-(benzoylamino-methyl)-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl]-2-methyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester as a white solid (35 mg), m/z=538 (M+H).

Workup

  1. additionwere added
  2. customThe reaction mixture was partitioned between water and DCM
  3. washthe organic layer was then washed with water (30 mL×2) and brine (30 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by preparative-HPLC (acetonitrile and NH4OAc]

Sources & evidence

ORD record
ord-7acdf076e2ff4260bf94a0060721c731
Source dataset
uspto-grants-2016_05
Patent number
US09340573B2

Reaction notes

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