تفاعل #1483077

ord-7d57691e8f6b4d8ca9c8631a0e278a01

معادلة التفاعل

COC(=O)c1ccc2c(c1)c(Cc1ccc(NC(=O)c3ccccc3)cc1)cn2C
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
CO
methanol
O
water
Cn1cc(Cc2ccc(NC(=O)c3ccccc3)cc2)c2cc(C(=O)O)ccc21
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid
المردود 98.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزconcentrated in vacuo
  2. 2
    workup.ADDITIONThe remaining residue was diluted with ethyl acetate (20 mL)
  3. 3
    غسيلwashed with 1N HCl (20 mL)
  4. 4
    تجفيفThe organic layer was dried over MgSO4
  5. 5
    ترشيحfiltered
  6. 6
    تركيزconcentrated

الإجراء التجريبي

A solution of 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 0.17 mmol), sodium hydroxide (21 mg, 0.52 mmol), methanol (3 mL), water (1 mL) and THF (3 mL) was heated to 60° C. for 24 hr. The reaction solution was then cooled to room temperature and concentrated in vacuo. The remaining residue was diluted with ethyl acetate (20 mL) and washed with 1N HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid (64 mg, 98% yield).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08900565B2uspto-grants-2014_12