Triethylamine → HCID 59732054, compound

HRID 2378603Notes

Reaction equation

HRID 2378603 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][C:7]=1[CH2:21]O.C(N(CC)CC)C.CS([Cl:46])(=O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][C:7]=1[CH2:21][Cl:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59731985HCID 59731985, compound

Product 1

HCID 59732054HCID 59732054, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(2-Hydroxymethyl-4-tert-butoxycarbonylamino-5-methyl-phenyl)-2-(R)-benzyloxycarbonylamino-propionic acid methyl ester (510 mg, 1.1 mmol) was dissolved in dichoromethane (5 mL). Triethylamine (250 μL, 1.8 mmol ) was added to the mixture followed by methanesulfonyl chloride (100 μL, 1.3 mmol). Mixture was stirred at room temperature for 1.5 hours. Mixture was diluted with dichloromethane then washed once with water, twice with 1N hydrochloric acid, and once with brine. Organics were dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as white solid in 91% yield. MS m/e (M+H)+=491.

Workup

  1. washthen washed once with water, twice with 1N hydrochloric acid
  2. dry with materialOrganics were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-954c998e6db942729af351c1dcfffec3
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

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