Triethylamine → HCID 59588983, compound

HRID 1969321Notes

Reaction equation

HRID 1969321 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8]/[CH:9]=[C:10](/[F:13])\[CH2:11][OH:12])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:12][CH2:11]/[C:10](/[F:13])=[CH:9]\[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23394352HCID 23394352, compound

Product 1

HCID 59588983HCID 59588983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of (E)-tert-butyl-N-(3-fluoro-4-hydroxybut-2-enyl)carbamate (1.65 g, 8 mmol) in CH2Cl2 (30 mL) at 0° C. under nitrogen was added triethylamine (1.67 mL, 12 mmol) followed by methanesulfonyl chloride (0.74 mL, 9.6 mmol). The reaction was left to stir at 0° C. for 1 hr. All volatiles were removed under reduced pressure and the crude yellow residue was taken up in acetone (30 mL). The insoluble white precipitate (triethylammonium chloride) was filtered off and washed with acetone (10 mL). The filtrate containing the crude mesylate was used immediately for Procedure E.

Workup

  1. waitThe reaction was left
  2. customAll volatiles were removed under reduced pressure
  3. filtrationThe insoluble white precipitate (triethylammonium chloride) was filtered off
  4. washwashed with acetone (10 mL)
  5. additionThe filtrate containing the crude mesylate

Sources & evidence

ORD record
ord-349ef3ae0eb04c5b964bf341a7b694f8
Source dataset
uspto-grants-2013_04
Patent number
US08426587B2

Reaction notes

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