2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 131719656, compound

HRID 1900903Notes

Reaction equation

HRID 1900903 reaction equation
C(O)(=O)C.[C:5]([C:8]1[CH:32]=[CH:31][C:11]([C:12]([NH:14][C:15](=[O:30])[NH:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:13])=[CH:10][CH:9]=1)(=[NH:7])[NH2:6].O.[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37]>CO>[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37].[C:5]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15](=[O:30])[NH:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[O:13])=[CH:31][CH:32]=1)(=[NH:6])[NH2:7].[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([C:5](=[NH:6])[NH2:7])=[CH:32][CH:31]=2)=[O:30])=[CH:29][CH:28]=1)[CH3:27]

Participants

4

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 131719657HCID 131719657, compound

Product 1

HCID 131719656HCID 131719656, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
10 °C

Procedure

To a suspension of ethyl 4-[3-(4-amidinobenzoyl)ureido]phenoxyacetate, acetate salt (100 mg), in methanol (5 ml) was added a solution of citric acid monohydrate (47 mg) in methanol (1 ml). The resultant mixture was sonicated for 5 minutes and then heated to boiling. The resultant solution was filtered hot. On cooling to 10° C., a solid precipitated which was collected, washed with methanol and ether, and dried to give the title compound (57 mg) as a white crystalline solid: m.p. 198°-200° C. (decomposes); NMR Spectrum (DMSO-d6) 1.23 (3H, t), 2.41 (2H, q), 4.18 (2H, q), 4.77 (2H, s), 6.94 (2H, d), 7.50 (2H, d), 7.94 (2H, d), 8.18 (2H, d), 10.30 (4H, br s), 10.60 (1H, s); Elemental Analysis: calculated for C19H20N4O5. 0.5 C6H8O7. 0.33 H2O: C, 54.3%; H, 5.11%; N, 11.5%; found: C, 54.5%; H, 5.1%; N, 11.4%.

Workup

  1. temperatureheated to boiling
  2. filtrationThe resultant solution was filtered hot
  3. customa solid precipitated which
  4. customwas collected
  5. washwashed with methanol and ether
  6. customdried

Sources & evidence

ORD record
ord-0ec9e031d13f488fae22f70ab9a8f46c
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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