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

HRID 2084931Notes

Reaction equation

HRID 2084931 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-9c02a0962fe743a98129bc2f631f95c2
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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