Sodium Hydroxide → Glycine, N-(3-((mercaptoacetyl)amino)benzoyl)-, monosodium salt, hydrate (2:7)

HRID 839047Notes

Reaction equation

HRID 839047 reaction equation
[OH-].[Na+:2].[SH:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[O:12])=[O:6]>O1CCCC1>[Na+:2].[SH:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[C:11]([NH:13][CH2:14][C:15]([O-:17])=[O:16])=[O:12])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 49990HCID 49990, compound

Product 1

HCID 23703976Glycine, N-(3-((mercaptoacetyl)amino)benzoyl)-, monosodium salt, hydrate (2:7)Yield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of 10% sodium hydroxide (65 ml., 0.1625 mole) is slowly added to a suspension of N-[3-(mercaptoacetylamino)benzoyl]glycine (43 g., 0.16 mole) in 230 ml. of tetrahydrofuran with cooling at 10°-20° C. The mixture is warmed to about 20°-25° C. and filtered from a trace of solid. Diluting the filtrate with 480 ml. of tetrahydrofuran promotes the formation of a suspension which is stirred for 2 hr. and collected. The collected material is washed with tetrahydrofuran and air dried to provide 50 g. (88.3% yield) of N-[3-(mercaptoacetylamino)benzoyl]glycine sodium salt hydrated with 3.5 moles water, m.p. 68°-120° C. (dec.).

Workup

  1. temperatureThe mixture is warmed to about 20°-25° C.
  2. filtrationfiltered from a trace of solid
  3. additionDiluting the filtrate with 480 ml
  4. customand collected
  5. washThe collected material is washed with tetrahydrofuran and air
  6. customdried
  7. customto provide 50 g

Sources & evidence

ORD record
ord-782bfd7337c148d59b5bf7ff28d02a05
Source dataset
uspto-grants-1978_06
Patent number
US04093739

Reaction notes

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