Benzenesulfonyl chloride → HCID 86604862, compound

HRID 1431997Notes

Reaction equation

HRID 1431997 reaction equation
[CH:1]#[C:2][CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6].C([O-])([O-])=O.[Na+].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1.O>[CH:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:21]([NH:8][C@H:4]([CH2:3][C:2]#[CH:1])[C:5]([OH:7])=[O:6])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 6992713D-Propargylglycine

Product 1

HCID 86604862HCID 86604862, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of d-propargylglycine (32.10 g, 88.46 mmol), Na2CO3 (20.62 g, 194.6 mmol), and benzenesulfonyl chloride (18.74 g, 106.2 mmol) in p-dioxane/H2O (1:1, 200 ml) was stirred overnight at rt. The reaction mixture was concentrated and the ph adjusted to 4.0 with 10% hcl. The aqueous layer was extracted with CHCl3 (3×), dried over mgso4, and concentrated to give the title compound. 1H NMR (400 mhz, CDCl3): δ 2.04 (s, 1h), 2.65 (s, 3h), 2.71 (m, 2h), 4.11 (m, 1h), 5.61 (d, 8.4 hz, 1h), 7.61 (m, 3h), 7.88 (m, 2h).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous layer was extracted with CHCl3 (3×)
  3. customdried over mgso4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e363474b47344c638cafe53a19fcca7a
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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