Methanol → HCID 60073590, 화합물

HRID 49972노트

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HRID 49972 반응식
C([N:8]1[CH2:15][C@@H:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])(OC(C)(C)C)=O.O=S(Cl)Cl.[CH3:29]O>>[CH3:29][O:12][C:10](=[O:11])[C@@H:9]1[CH2:13][C@H:14]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:15][NH:8]1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21301022cis-N-Boc-4-(4-bromobenzyl thio)-L-proline

생성물 1

HCID 60073590HCID 60073590, 화합물

실험 절차

To a solution of Na (0.25 g) (0.011 mol) in 3 mL of MeOH was added 4-bromobenzyl mercaptan (2.2 g) (0.011 mol). The reaction mixture was stirred for 1 h. Trans-N-Boc-4-methanesulfonyloxy-L-proline methyl ester (1.2 g) (0.0037 mol) (Preparation 9) was added and the mixture refluxed for 18 hrs. Upon cooling to RT, 40 mL of water was added and the mixture was extracted with EtOAc. The aqueous layer was acidified with 1 N HCl and extracted with DCM. The combined organic extracts were washed with water, dried over MgSO4, and the solvent evaporated in vacuo to afford cis-N-Boc-4-(4-bromobenzyl thio)-L-proline (1.08 g). NMR (CDCl3, 200 MHz): 10.65 (1H, COOH), 7.4 (2H, d), 7.15 (2H, d), 4.15-4.35 (1H, m), 3.65 (2H, s), 2.95-3.35 (2H, m), 2.4-2.6 (1H, m), 1.85-2.2 (1H, m), 1.3-1.5 (9H). To a solution of cis-N-Boc-4-(4-bromobenzyl thio)-L-proline (1.08 g) in 10 mL of MeOH was added dropwise SOCl2 (0.2 mL), and the mixture was stirred for 72 hrs at RT. The solvent was evaporated under reduced pressure and the residue dissolved in DCM. The organic layer was washed with dilute aqueous NaHCO3, water, and dried over MgSO4. The solvent was evaporated in vacuo to afford cis-4-(4-bromo-benzylthio)-L-proline methyl ester (0.6 g).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in DCM
  3. washThe organic layer was washed with dilute aqueous NaHCO3, water
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-f76ece27eac14671935cbcca708c970c
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

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