Trifluoroacetic acid → 2-(5-((4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

HRID 471028ノート

反応式

HRID 471028 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH2:31][N:32]2[CH2:50][CH2:49][C:35]3([O:40][CH2:39][CH2:38][N:37]([C:41]([C:43]4[S:44][C:45]([CH3:48])=[CH:46][CH:47]=4)=[O:42])[CH2:36]3)[CH2:34][CH2:33]2)[S:29][CH:30]=1.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:48][C:45]1[S:44][C:43]([C:41]([N:37]2[CH2:36][C:35]3([CH2:49][CH2:50][N:32]([CH2:31][C:28]4[S:29][CH:30]=[C:26]([CH2:25][CH:24]=[O:23])[CH:27]=4)[CH2:33][CH2:34]3)[O:40][CH2:39][CH2:38]2)=[O:42])=[CH:47][CH:46]=1

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989018(9-((4-(2-Hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

生成物 1

HCID 579891582-(5-((4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Dess-Martin periodinane (0.35 g) was added to a stirred solution of (9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone (example 27, step d) (0.19 g) and trifluoroacetic acid (0.052 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.07 mL) was added, the solution dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.19 g. Used directly.

後処理

  1. customseparated
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine
  3. additionAcetic acid (0.07 mL) was added
  4. dry with materialthe solution dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo (bath temperature ˜30° C.)

出典と根拠

ORDレコード
ord-5f6b873428f241b9b469f8c40a772470
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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