Diethyl Ether → HCID 10247436, compound

HRID 751007Notes

Reaction equation

HRID 751007 reaction equation
[CH2:1]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=O)C1C=CC=CC=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28].C1([O:39]C(=O)OC2C=CC=CC=2)C=CC=CC=1.C(OCC)C>C1(C)C(O)=CC=CC=1>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([N:8]2[CH2:9][C:10](=[O:12])[N:23]([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([OH:29])=[O:28])[C:1]2=[O:39])=[CH:18][CH:17]=1)([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74193-Aminobenzoic AcidHCID 7597Diphenyl carbonateHCID 39417193HCID 39417193, compound

Product 1

HCID 10247436HCID 10247436, compound

Reagents, catalysts & solvents 1

HCID 335O-CresolSolvent

Procedure

A solution of benzyl-N-(4-tert-butylphenyl)glycine (1.20 g, 4.04 mmol), 3-aminobenzoic acid (0.55 g, 4.01 mmol) and diphenylcarbonate (0.87 g, 4.06 mmol) in cresol (4 mL) was heated to reflux for 5 h. The mixture was cooled, poured into 20 mL diethyl ether, and filtered. The solid product as named in the title was dried under vacuum (1.10 g, 3.12 mmol, 78%). m.p. 256-258° C. 1H NMR (d6-DMSO, 300 MHz): δ 8.01 (1H, t, J=2 Hz), 7.98 (1H, dt, J=8, 2 Hz), 7.70-7.62 (2H, m), 7.60 (2H, d, J=8 Hz), 7.43 (2H, d, J=8 Hz), 4.60 (2H, s), 1.28 (9H, s). Mass spectrum (ES+): m/z 354 (23), 353 (100). Elemental analysis: calculated for C20H20N2O4 C 68.07, H 5.85, N 7.61; observed C 68.17, H 5.72, N 7.95.

Workup

  1. temperatureto reflux for 5 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customwas dried under vacuum (1.10 g, 3.12 mmol, 78%)

Sources & evidence

ORD record
ord-bc1ec2fe1f134285ac0f96f52319af6e
Source dataset
uspto-grants-2008_07
Patent number
US07405233B2

Reaction notes

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