5-Amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid → (S)-(-)-5-[(2-Acetoxypropanoyl)amino]-2,4,6-triiodoisophthalic Acid

HRID 76840

반응식

HRID 76840 반응식
[C:1]([O:4][C@@H:5]([CH3:9])[C:6](Cl)=[O:7])(=[O:3])[CH3:2].[NH2:10][C:11]1[C:12]([I:25])=[C:13]([C:22]([OH:24])=[O:23])[C:14]([I:21])=[C:15]([C:19]=1[I:20])[C:16]([OH:18])=[O:17]>CC(N(C)C)=O>[C:1]([O:4][C@@H:5]([CH3:9])[C:6]([NH:10][C:11]1[C:19]([I:20])=[C:15]([C:16]([OH:18])=[O:17])[C:14]([I:21])=[C:13]([C:12]=1[I:25])[C:22]([OH:24])=[O:23])=[O:7])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 30157835-Amino-2,4,6-triiodo-1,3-benzenedicarboxylic acidHCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetate

생성물 1

HCID 15817302(S)-(-)-5-[(2-Acetoxypropanoyl)amino]-2,4,6-triiodoisophthalic Acid수율 81%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
50 °C

실험 절차

(S)-1-chloro-1-oxopropan-2-yl acetate (37.4 ml, 295.4 mmol) was added slowly to a suspension of 5-amino-2,4,6-triiodoisophthalic acid (50.0 g, 89.5 mmol) in DMA (100 ml) at a temperature of between 25° C. and 29° C. The resulting mixture was heated to about 50° C. and stirred at this temperature for about 8 hours after which heating was removed and the mixture was stirred for about 14 hours at room temperature. The reaction mixture was added slowly over water (500 ml) with strong stirring at a temperature between 22° C. and 30° C. After addition 300 ml of water were added to the suspension. The suspension was stirred for 5 further hours at about 22° C. after which the white solid was filtered and washed with water previously cooled at about 5° C. twice (30 ml each time). The product was dried in a vacuum oven at about 5.0° C. to yield (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid (48.8 g, 72.5 mmol).

후처리

  1. temperatureheating
  2. customwas removed
  3. stirringthe mixture was stirred for about 14 hours at room temperature
  4. additionThe reaction mixture was added slowly over water (500 ml)
  5. stirringwith strong stirring at a temperature between 22° C. and 30° C
  6. additionAfter addition 300 ml of water
  7. additionwere added to the suspension
  8. stirringThe suspension was stirred for 5 further hours at about 22° C. after which the white solid
  9. filtrationwas filtered
  10. washwashed with water
  11. temperaturepreviously cooled at about 5° C. twice (30 ml each time)
  12. customThe product was dried in a vacuum oven at about 5.0° C.

출처 및 근거

ORD 기록
ord-3de18174c3394887ab022402120c5a28
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835672B2

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