Dichloromethane → Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

HRID 1009144

反応式

HRID 1009144 の反応式
[Si:1]([O:8][C@H:9]([CH:27]=O)[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:29][C:30]1([CH3:46])[CH2:39][C@H:38]([NH2:40])[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=2)[NH:31]1.C(Cl)Cl.COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Si:1]([O:8][C@H:9]([CH2:27][NH:40][C@@H:38]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH:36]=2)[NH:31][C:30]([CH3:46])([CH3:29])[CH2:39]1)[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

参加物

6

反応物 5

HCID 6344DichloromethaneHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 67305468(S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amineHCID 86614118tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate

生成物 1

HCID 86614130Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

実験手順

To a solution of tert-butyl(2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate (0.148 g, 0.360 mmol) and (S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amine (0.0886 g, 0.360 mmol) in DCM (7.19 ml, 0.360 mmol) was added trimethoxymethane (0.394 ml, 3.60 mmol). The resulting solution was stirred for 1 hour at which time, sodium triacetoxyborohydride (0.229 g, 1.08 mmol) was added. The solution was then stirred for 30 minutes, quenched with saturated Rochelle's salt and stirred for an additional 20 minutes. The mixture was transferred to a sep. funnel containing DCM and H2O. The aqueous layer was washed 4× with DCM. The organic layers were combined, washed 1× with brine, dried with MgSO4, filtered and concentrated to afford the title compound. MS m/z: 642 (M+1).

後処理

  1. additionwas added
  2. customquenched with saturated Rochelle's salt
  3. stirringstirred for an additional 20 minutes
  4. additionfunnel containing DCM and H2O
  5. washThe aqueous layer was washed 4× with DCM
  6. washwashed 1× with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-626e34d0e584403484c0ce8261009f94
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

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