Benzilic acid → HCID 69939075, 화합물

HRID 1058292

반응식

HRID 1058292 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[C@@H:15]1[CH2:19][CH2:18][CH2:17][NH:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26](O)(=[O:41])[C:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28].CN1CCOCC1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:29]1([C:27]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([OH:28])[C:26]([N:16]2[CH2:17][CH2:18][CH2:19][C@H:15]2[C:14]([NH:13][CH2:12][C:11]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:10]=2[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:20])=[O:41])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

6

반응물 4

HCID 6463Benzilic acidHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11428605HCID 11428605, 화합물

생성물 1

HCID 69939075HCID 69939075, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide (0.17 g, 0.45 mmol) in DMF (1 mL) was added benzilic acid (0.23 g, 0.51 mmol), N-methylmorpholine to pH=8 (as measured on wetted E. Merck pH indicator strips), and BOP reagent (0.31 g, 0.70 mmol). After 1 hour of mixing at room temperature, HPLC analysis indicated complete consumption of the starting amine. The mixture was filtered and purified on a preparative HPLC. Pure fractions were pooled and lyophilized to yield 1-(2,2-diphenyl-2-hydroxyethanoyl)-N-(2-tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)-L-prolinamide as a solid (0.23 g, HPLC RT=3.75 min, method A; LC-MS m/z=578).

후처리

  1. additionAfter 1 hour of mixing at room temperature
  2. customconsumption of the starting amine
  3. filtrationThe mixture was filtered
  4. custompurified on a preparative HPLC

출처 및 근거

ORD 기록
ord-0a3a9ca4e0f14fd4a2ac9feded599da8
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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