Sodium Carbonate → HCID 23326541, compound

HRID 355199Notes

Reaction equation

HRID 355199 reaction equation
[CH2:1]([O:8][C:9]1(O)[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][CH:10]1[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[C:11]([C:10]1[CH:14]=[C:15]([CH:16]=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:18]([OH:21])[CH2:19][NH:23][CH2:24][CH2:25][CH2:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1)(=[O:12])[NH2:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 42201883-(benzotriazol-1-yl)propan-1-amineHCID 86738829HCID 86738829, compound

Product 1

HCID 23326541HCID 23326541, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 17.5 gm of 2-benzyloxy-5-bromoacetyl salicylamide, 17.6 gm of 1-(3-aminopropyl)-1H-benzotriazole, 6 gm of sodium carbonate and 150 ml of ethyl acetate was refluxed for 1.5 hours. After separation of the inorganic constituents, the mother liquor was evaporated, the residue was dissolved in a 100 ml of acetonitrile, and the solution was acidified with 5 gm of oxalic acid. The precipitated 1-[3-(3-carbamoyl-4-benzyloxy-β-oxophenethylamino)-propyl]-1-H-benzotriazole oxalate was collected by suction of filtration converted with aqueous ammonia into the base (m.p. 186°-188° C.) and reduced in 100 ml of ethanol with sodium borohydride to form 1-[3-(3-carbamoyl-4-benzyloxy-β-hydroxyphenethylamino)propyl]-1-H-benzotriazole.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. customAfter separation of the inorganic constituents
  3. customthe mother liquor was evaporated
  4. dissolutionthe residue was dissolved in a 100 ml of acetonitrile
  5. filtrationThe precipitated 1-[3-(3-carbamoyl-4-benzyloxy-β-oxophenethylamino)-propyl]-1-H-benzotriazole oxalate was collected by suction of filtration

Sources & evidence

ORD record
ord-ab40dc0e13c24894a680bb3360df91e3
Source dataset
uspto-grants-1983_03
Patent number
US04378361

Reaction notes

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