Triethylamine → HCID 19689398, compound

HRID 1291880Notes

Reaction equation

HRID 1291880 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15]>ClCCl>[N:8]1[CH:5]=[CH:4][C:14]([N:16]2[CH2:19][CH2:20][CH:6]([CH2:7][C:2]([O:1][C:2]3[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=3)=[O:1])[CH2:18][CH2:17]2)=[CH:15][CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 422581Methyl 2-((4-hydroxyphenyl)amino)acetate

Product 1

HCID 19689398HCID 19689398, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of the foam in dry dichloromethane (5 ml) was added dropwise to a stirred solution of methyl N-(4-hydroxyphenyl)glycinate (210 mg) and triethylamine (0.33 ml) in dry dichloromethane (10 ml) and the mixture stirred for 16 hours. The mixture was diluted with dichloromethane, washed with water, dried and evaporated. Purification by flash chromatography on silica, eluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether gave the title compound, 80 mg, as a white solid: m.p. 120°-122° C.; NMR(d6DMSO), δ 8.13(2H,d), 6.84(2H,d), 6.81(2H,d), 6.54(2H,d), 6.01(1H,t), 3.96(2H,bd), 3.90(2H,d), 3.66(3H,s), 2.90(2H,dt), 2.50(2H,d +DMSO), 2.07(1H,m), 1.81(2H,bd), 1.30(2H,dq); m/e 384(M+H)+ ; calculated for C21 H25N3O4. 0.5 H2O: C, 64.3; H, 6.6; N, 10.7. found: C, 64.2; H, 6.3; N, 10.7%.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customPurification by flash chromatography on silica
  5. washeluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether

Sources & evidence

ORD record
ord-a5d2c43c4b0c4bddb525bc809af658b9
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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