Triethylamine → HCID 21107410, compound

HRID 1765528Notes

Reaction equation

HRID 1765528 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][OH:31])=[CH:23][C:8]=1[C:9]([NH:11][CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:10].C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][O:31][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][C:8]=1[C:9]([NH:11][CH2:12][C:13]12[CH2:20][CH:19]3[CH2:18][CH:17]([CH2:16][CH:15]([CH2:21]3)[CH2:14]1)[CH2:22]2)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69483573HCID 69483573, compound

Product 1

HCID 21107410HCID 21107410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonylchloride (0.08 mL) was added to a solution of 2-chloro-5-[(3S)-3,4-dihydroxybutyl]-N-(tricyclo(3.3.1.13,7]dec-1-ylmethyl)benzamide (Example 1b) (0.33 g) and triethylamine (0.33 ml) in dichloromethane (10 mL). After 1 hour the reaction mixture was concentrated, redissolved in ethyl acetate and the organic layer washed with water, brine, dried over anhydrous magnesium sulfate, filtered and evaporated. Purification by normal phase HPLC (gradient 0–5% ethanol (EtOH) in dichloromethane on silica Novapak™ column), gave the sub-titled compound (0.14 g).

Workup

  1. concentrationAfter 1 hour the reaction mixture was concentrated
  2. dissolutionredissolved in ethyl acetate
  3. washthe organic layer washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by normal phase HPLC (gradient 0–5% ethanol (EtOH) in dichloromethane on silica Novapak™ column)

Sources & evidence

ORD record
ord-f752a2f6aa654cfa968a59b808058688
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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