Glyoxylic Acid → [(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid

HRID 12238

반응식

HRID 12238 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@@H:18]3[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[CH2:20][NH:19]3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.C(N(CC)CC)C.C([BH3-])#N.[Na+].[C:37]([OH:41])(=[O:40])[CH:38]=O>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:16]([C@H:18]3[N:19]([CH2:38][C:37]([OH:41])=[O:40])[CH2:20][C:21]([CH3:25])([CH3:24])[O:22][CH2:23]3)=[O:17])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

참가 물질

7

반응물 4

HCID 760Glyoxylic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 67165625(S)-6,6-Dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

생성물 1

HCID 11384512[(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-acetic acid수율 72%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a suspension of (S)-6,6-Dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide (2.6 g, 6.0 mmoles) in 60 ml of methanol was added 1.7 ml of triethylamine (2.0 eq.), sodium cyanoborohydride (575 mg, 9.1 mmoles) and glyoxylic acid (780 mg, 8.5 mmoles). The reaction mixture was stirred at ambient temperature for 1.5 hrs. Water was added (5 ml) and the mixture was concentrated to a thick yellow slurry. More water was then added (30 ml) and the resulting slurry was stirred at ambient temperature for 10 min. and was filtered. The collected yellow solid was washed with water and dried under high vacuum to give 1.80 g (71%) of the desired product.

후처리

  1. concentrationthe mixture was concentrated to a thick yellow slurry
  2. additionMore water was then added (30 ml)
  3. stirringthe resulting slurry was stirred at ambient temperature for 10 min.
  4. filtrationwas filtered
  5. washThe collected yellow solid was washed with water
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-5063a34e8e444b9699047499e466ff58
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727985B2

연결된 노트

불러오는 중…