Chlorotrimethylsilane → (2S,3S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide

HRID 1433786

反応式

HRID 1433786 の反応式
[NH2:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C@H:34]([OH:37])[CH2:35][OH:36])=[CH:28][CH:27]=1)[C:3]([NH:5][C@@H:6]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[Cl:17])=[O:8])=[O:4].C(N(CC)CC)C.Cl[Si:46]([CH3:49])([CH3:48])[CH3:47]>C(OCC)(=O)C>[NH2:1][C@H:2]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C@H:34]([O:37][Si:46]([CH3:49])([CH3:48])[CH3:47])[CH2:35][O:36][Si:46]([CH3:49])([CH3:48])[CH3:47])=[CH:28][CH:27]=1)[C:3]([NH:5][C@@H:6]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[Cl:17])=[O:8])=[O:4]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 69006543(2S,3S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide

生成物 1

HCID 69007900(2S,3S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,3S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide (330 mg, 0.44 mmol) in dry, degassed tetrahydrofuran (5 mL) were added triethylamine (277 μL, 1.98 mmol) and chlorotrimethylsilane (230 μL, 1.76 mmol) and the mixture stirred at ambient temperature for 30 minutes. The resulting suspension was diluted with ethyl acetate (50 mL) and washed with brine (2×50 mL). The combined brine layers were back extracted with ethyl acetate (2×50 mL), the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo to give crude (2S,3S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide which was of adequate purity for subsequent use in step 6 without additional purification (330 mg, 96%).

後処理

  1. customdegassed tetrahydrofuran (5 mL)
  2. washwashed with brine (2×50 mL)
  3. extractionThe combined brine layers were back extracted with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic layers dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6932d8c887654d449c7c94041be1265e
出典データセット
uspto-grants-2009_11
特許番号
US07612212B2

関連ノート

読み込み中…