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

HRID 2163248Notes

Reaction equation

HRID 2163248 reaction equation
[Na+:1].NCC([O-])=O.[OH-].[Na+].[SH:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])=[O:12]>O1CCCC1>[Na+:1].[SH:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=1)[C:17]([NH:19][CH2:20][C:21]([O-:23])=[O:22])=[O:18])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 49990HCID 49990, compoundHCID 4684308Sodium Glycinate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22.5 °C

Procedure

Stable Hydrate of N-[3-Mercaptoacetylamino)benzoyl]-glycine Sodium Salt.-- 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. filtrationfiltered from a trace of solid
  2. additionDiluting the filtrate with 480 ml
  3. customand collected
  4. washThe collected material is washed with tetrahydrofuran and air
  5. customdried
  6. customto provide 50 g

Sources & evidence

ORD record
ord-e5d8ca56bb1947da8c19646d1f714b94
Source dataset
uspto-grants-1979_01
Patent number
US04132803

Reaction notes

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