Water → N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

HRID 1976466Notes

Reaction equation

HRID 1976466 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:18]#[C:19][CH3:20].O>ClCCl>[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:6][CH:5]([CH2:7][OH:8])[C:4]([O:3][CH3:2])=[O:9])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:18]#[C:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 11446470D-Serine methyl ester hydrochloride

Product 1

HCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° solution of D-serine methyl ester hydrochloride (0.62 g, 4 mmol) in 5 mL of dichloromethane was added triethylamine (1.67 mL,12 mmol) followed by a dichloromethane (6 mL) solution of 4-(2-butynyloxy)-benzenesufonyl chloride (0.98 g, 4 mmol). The reaction was stirred at room temperature overnight and then the mixture was poured into water. The organic layer was washed with 2N citric acid, water and brine, dried over sodium sulfate, filtered and concentrated to give 1.16 g of methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate. Yield˜89.2%. mp 72-74° C. Electrospray Mass Spec 328.2 (M+H)+.

Workup

  1. washThe organic layer was washed with 2N citric acid, water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a06b10228bd44652b76be7bc7f7582ec
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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