Water → HCID 86724000, compound

HRID 1475388Notes

Reaction equation

HRID 1475388 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH2:17][OH:18])[N:13]=[CH:12][C:11]=2[C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH2:17][O:18][S:29]([CH3:28])(=[O:31])=[O:30])[N:13]=[CH:12][C:11]=2[C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70980657HCID 70980657, compound

Product 1

HCID 86724000HCID 86724000, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 6-hydroxymethyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.268 g, 0.96 mmol) and triethylamine (0.417 mL, 3 mmol) in EtOAc (4.8 mL) was added methanesulfonyl chloride (0.224 mL, 2.9 mmol) at 0° C. The reaction was stirred at the same temperature for 1 h. Water (5 mL) was added and the aqueous mixture extracted with EtOAc (3×5.0 mL). The combined organic extracts were washed with brine (20 mL), dried over sodium sulfate, filtered and the solvent removed in vacuo to give the title compound (0.279 g,) as a pale yellow oil. MS: [M+H]+=357.

Workup

  1. extractionthe aqueous mixture extracted with EtOAc (3×5.0 mL)
  2. washThe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2f575b0da27e49769d9e5c7f29371d78
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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