Ethyl chloroformate → HCID 69585940、化合物

HRID 1242073ノート

反応式

HRID 1242073 の反応式
Cl.[O:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH:8]([CH2:12][N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])[CH2:7]2)[O:5][CH2:4][CH2:3]1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:28]([O:27][C:25]([N:9]1[CH2:10][CH2:11][C:6]2([O:5][CH2:4][CH2:3][O:2]2)[CH2:7][CH:8]1[CH2:12][N:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22])=[O:26])[CH3:29]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 21936741HCID 21936741、化合物

生成物 1

HCID 69585940HCID 69585940、化合物収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of the above 2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione hydrochloride (0.7 g, 2.1 mmol) and ethyl chloroformate (0.24 ml, 2.5 mmol) in dry tetrahydrofuran (14 ml) cooled in an ice bath under nitrogen was added diisopropylethylamine (0.95 ml, 5.4 mmol) and the reaction mixture was stirred at ambient temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between dichloromethane (25 ml) and 1N hydrochloric acid (25 ml). The layers were separated, and the aqueous layer extracted with dichloromethane (20 ml). The combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was triturated with n-butylchloride, filtered and dried with nitrogen which afforded 0.47 g (61%) of 7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid ethyl ester.

後処理

  1. temperaturecooled in an ice bath under nitrogen
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between dichloromethane (25 ml) and 1N hydrochloric acid (25 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with dichloromethane (20 ml)
  6. washThe combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo
  10. customThe residue was triturated with n-butylchloride
  11. filtrationfiltered
  12. customdried with nitrogen which

出典と根拠

ORDレコード
ord-75d77856c5284fedbda7ee5bcd310080
出典データセット
uspto-grants-2006_10
特許番号
US07115624B1

反応ノート

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