Oxalyl chloride → 2-[(5,6,7,8-Tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

HRID 1047693노트

반응식

HRID 1047693 반응식
[C:1]1([C:11]([OH:13])=O)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:20]([O:22][C:23]([C:25]1([NH2:34])[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26]1)=[O:24])[CH3:21].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:20]([O:22][C:23]([C:25]1([NH:34][C:11]([C:1]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:13])[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26]1)=[O:24])[CH3:21]

참가 물질

6

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acidHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

생성물 1

HCID 593141592-[(5,6,7,8-Tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester수율 59.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (500 mg, 2.84 mmol) in DCM (10 mL) is added oxalyl chloride (0.50 mL, 5.68 mmol) dropwise. The resulting solution is stirred at RT for 2 h. After the removal of DCM and excess oxalyl chloride, the residue, 2-amino-indan-2-carboxylic acid ethyl ester (583 mg, 2.84 mmol) and DIPEA (1.88 mL, 11.3 mmol) are dissolved in DCM (20 mL). The resulting solution is stirred overnight. The reaction solution is diluted with DCM (30 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-20% EtOAc in heptane) to give the pure product (37) as white solid (610 mg, 59%).

후처리

  1. customAfter the removal of DCM and excess oxalyl chloride
  2. stirringThe resulting solution is stirred overnight
  3. washwashed with water (1×5 mL) and brine (2×5 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-20% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-0d1454b282c44fb18e18a30d01d7592a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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