Dimethylformamide → 2-(Ethoxycarbonyl)cyclopropane-1-carboxylic acid

HRID 1941562

반응식

HRID 1941562 반응식
NN=CC1C=CC(N[C:11]([CH:13]2[CH2:15][CH:14]2[C:16]([OH:18])=[O:17])=[O:12])=CC=1.CN(C=O)C.[CH3:24][C:25](C)(C)C(Cl)=O.CN1CC[O:35]CC1>N1C=CC=CC=1>[CH2:24]([O:18][C:16]([CH:14]1[CH2:15][CH:13]1[C:11]([OH:12])=[O:35])=[O:17])[CH3:25]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 79724-MethylmorpholineHCID 62493Pivaloyl chlorideHCID 69949286HCID 69949286, 화합물

생성물 1

HCID 3174452-(Ethoxycarbonyl)cyclopropane-1-carboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
55 °C

실험 절차

t-Butyl-β(S)-[[[2-[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]cyclopropyl]carbonyl]amino]-phenylpropanoate 0.90 g (0.0036 mol) of 2-[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]cyclopropyl-carboxylic acid was treated with 50 mL dry DMF and the solvent removed at 55° C. To the remaining solid was added 60 mL DMF, 6 mL pyridine and 0.43 g (0.44 mL, 0.0036 mol) trimethylacetyl chloride. After 0.5 hr at room temperature the reaction mixture was heated at 55° C. for 0.5 hr then 0.93 g (0.004 mol) tert-butyl-3-amino-3-phenyl propionate and 0.36 g (0.40 mL, 0.004mol) N-methylmorpholine were added and the reaction allowed to proceed overnight. At this point volatiles were removed and the desired product isolated by preparative RPHPLC and lyophilized to give a diastereomeric mixture of t-butyl-β(S)-[[[2-[[[4-(aminoiminomethyl)phenyl]amino]carbonyl]cyclopropyl]carbonyl]amino]-3-phenylpropanoate as a white powder (150 mg); 1H HMR (300 MHz) (d6DMSO) δ1.19 (m, 2H), 1.28 (s), 1.31 (s, 9H), 2.21 (m, 2H), 2.65 (d, J=7.9 Hz), 2.66 (d, J=7.7 Hz, 2H), 5.2 (m, 1H), 7.32 (m, 5H), 7.78 (m, 4H), 8.86 (d, 1H, J=8.6 Hz), 8.95 (bs, 2H), 9.10 (bs, 2H), 10.74 (s), 10.80 (s, 1H); MS (FAB) 451.4 (MH+).

후처리

  1. customthe solvent removed at 55° C
  2. customAt this point volatiles were removed

출처 및 근거

ORD 기록
ord-f70e2ca3ece542cb93e3469a7d34006a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703125

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