Sodium Hydroxide → HCID 9905824, compound

HRID 1839175Notes

Reaction equation

HRID 1839175 reaction equation
C[O:2][C:3](=[O:24])[C:4]([CH3:23])([NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[O:15][C:14]=2[CH:22]=1)(=[O:9])=[O:8])[CH3:5].[OH-].[Na+]>O1CCCC1>[CH3:23][C:4]([NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[O:15][C:14]=2[CH:22]=1)(=[O:9])=[O:8])([CH3:5])[C:3]([OH:24])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69890914HCID 69890914, compound

Product 1

HCID 9905824HCID 9905824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionic acid methyl ester (586 mg, 1.67 mmol) was suspended in aqueous tetrahydrofuran (1:1, 22 mL) and treated with aqueous sodium hydroxide (1 M, 7 mL). The reaction mixture was stirred at room temperature for 3 days. The tetrahydrofuran was concentrated in vacuo. The aqueous suspension was diluted with water (40 mL) and washed with diethyl ether. The aqueous phase was separated from the organic phase, and acidified (to a pH of 1). The resulting precipitate was collected by filtration and oven dried to give 2-methyl-2-(6,7,8,9-tetrahydro-dibenzofuran-3-sulfonylamino)-propionic acid (a compound of general Formula VIII) (457 mg, 81%), the structure of which is shown below. The melting point of this compound was determined to be 237-240° C. 1HNMR (DMSO-d6): δ8.0 (s, 1H), 7.8 (s, 1H), 7.6 (m, 2H), 2.7(m, 2H), 2.6 (m, 2H), 1.8 (m, 4H), 1.1 (s, 6H) ppm.

Workup

  1. concentrationThe tetrahydrofuran was concentrated in vacuo
  2. additionThe aqueous suspension was diluted with water (40 mL)
  3. washwashed with diethyl ether
  4. customThe aqueous phase was separated from the organic phase
  5. filtrationThe resulting precipitate was collected by filtration and oven
  6. customdried

Sources & evidence

ORD record
ord-9a9c7ea5c0cd4d46852014301f4bc35d
Source dataset
uspto-grants-2004_01
Patent number
US06677355B1

Reaction notes

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