Triethylamine → HCID 59201679, compound

HRID 451872Notes

Reaction equation

HRID 451872 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]([CH3:10])([CH3:9])[CH2:6][O:7][CH3:8].CCN(CC)CC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([O:1][CH2:2][C@@H:3]([NH:11][C:12]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18])[CH2:4][C:5]([CH3:10])([CH3:9])[CH2:6][O:7][CH3:8])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59201321HCID 59201321, compound

Product 1

HCID 59201679HCID 59201679, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of (S)-tert-butyl 1-hydroxy-5-methoxy-4,4-dimethylpentan-2-ylcarbamate (7.8 g, 30 mmol) in methylene chloride (150 mL) and Et3N (10.4 mL, 75 mmol) was cooled to −20° C., MsCl (6.9 g, 60 mmol) was added with fast dropwise addition maintaining the internal temperature at −20° C. The reaction mixture was stirred for 1 h in rt. The reaction was quenched with water (100 mL), extracted with CH2Cl2 (3×100 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give (S)-2-(tert-butoxycarbonylamino)-5-methoxy-4,4-dimethylpentyl methanesulfonate (10.1 g, 100%) as an oil that was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d275e1c0b25f4c6898bdfce81e860d44
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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