Triethylamine → HCID 59737240, compound

HRID 1907734

Reaction equation

HRID 1907734 reaction equation
[C:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:16][C:14](=O)[CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[NH2:20][CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1.C(N(CC)CC)C>N1C=CC=CC=1>[CH2:4]([O:3][C:1]([NH:11][C@H:12]1[CH2:13][C:14](=[O:16])[N:20]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:29][CH:30]=2)[C:17]1=[O:18])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 105553Benzoic acid, 4-(aminomethyl)-, hydrochloride (1:1)HCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Product 1

HCID 59737240HCID 59737240, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N-carbobenzyloxy-L-aspartic anhydride (236) (546 mg, 2.19 mmol) and 4-(aminomethyl)benzoic acid hydrochloride (237) (383 mg, 2.53 mmol) was suspended in pyridine (8 mL) and treated with triethylamine (1 mL). The white suspension was stirred at room temperature for 9 h then concentrated under reduced pressure. The residue was dissolved in acetic acid and stirred at 83° C. for 24 h, concentrated, diluted with DCM, washed with an aqueous solution of KHSO4 and H2O then concentrated. The residue was diluted once again with benzene, concentrated and the remaining yellow solid was triturated with MeOH/H2O (1:1) to give title compound 238 (471 mg, 56% yield).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in acetic acid
  3. stirringstirred at 83° C. for 24 h
  4. concentrationconcentrated
  5. additiondiluted with DCM
  6. washwashed with an aqueous solution of KHSO4 and H2O
  7. concentrationthen concentrated
  8. additionThe residue was diluted once again with benzene
  9. concentrationconcentrated
  10. customthe remaining yellow solid was triturated with MeOH/H2O (1:1)

Sources & evidence

ORD record
ord-c2f7d38c83c24b9eaac0d19eb909aacc
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Linked notes

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