Citric Acid → 3-({[(Tert-butoxy)carbonyl]amino}methyl)-5-nitrobenzoic acid

HRID 964487노트

반응식

HRID 964487 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][NH2:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10])([O-:3])=[O:2].[OH-].[Na+].[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)(C)(C)C.O>[C:22]([O:21][C:19]([NH:15][CH2:14][C:6]1[CH:7]=[C:8]([CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:9]([OH:11])=[O:10])=[O:18])([CH3:25])([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 19077132Methyl 3-(aminomethyl)-5-nitrobenzoate

생성물 1

HCID 190771343-({[(Tert-butoxy)carbonyl]amino}methyl)-5-nitrobenzoic acid수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

A solution of methyl 5-nitro-3-aminomethybenzoate (1980 mg, 9.4 mmol) in 1N NaOH (28 mL, 28 mmol) and tert-BuOH (20 mL) was stirred at r.t. for 10 hours and then added BOC2O (4100 mg, 18.8 mmol) and stirred for 17 hours. The reaction mixture was added hexanes (50 mL) and water (50 mL). The aqueous layer was acidified with 5% citric acid aq. and extracted with CH2 Cl2 (2×70 mL). The CH2Cl2 layers were combined and washed with water (50 mL). The organic layer was evaporated to give the desired compound (2450 mg, 88%): 1H NMR (300 MHz, DMSO-d6) δ 13.725 (s, 1H), 8.476 (s, 1H), 8.307 (s, 1H), 8.216 (s, 1H), 7.639 (t, J=5.7 Hz, 1H), 4.398 (d, J=5.7 Hz, 2H), 1.385 (s, 9H); 13C NMR (300 MHz, DMSO-d6) δ 165.5, 155.9, 147.9, 143.5, 133.6, 132.5, 125.4, 122.2, 78.3, 42.6, 28.2.

후처리

  1. extractionextracted with CH2 Cl2 (2×70 mL)
  2. washwashed with water (50 mL)
  3. customThe organic layer was evaporated

출처 및 근거

ORD 기록
ord-991de5e9c97e490b943c2a4013aaa6de
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770380

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