Triethylamine → 1-[(6-tert-Butoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-ethoxycarbonylpiperazine

HRID 352851

反応式

HRID 352851 の反応式
[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=O)=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([S:32]([N:35]1[CH2:40][CH2:39][NH:38][CH:37]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:36]1)(=[O:34])=[O:33])[CH:26]=[CH:25]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[C:1]([O:5][C:6]([CH:8]1[NH:13][CH2:12][C:11]2[S:14][C:15]([C:17]([N:38]3[CH2:39][CH2:40][N:35]([S:32]([C:27]4[CH:26]=[CH:25][C:24]5[C:29](=[CH:30][CH:31]=[C:22]([Cl:21])[CH:23]=5)[CH:28]=4)(=[O:34])=[O:33])[CH2:36][CH:37]3[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:19])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 227094496-Boc-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acidHCID 227100751-[(6-Chloronaphthalen-2-yl)sulfonyl]-3-ethoxycarbonylpiperazine hydrochloride

生成物 1

HCID 227095171-[(6-tert-Butoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-ethoxycarbonylpiperazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In N,N-dimethylformamide (30 ml), 6-tert-butoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid (WO94/21599) (742 mg), 1-[(6-chloronaphthalen-2-yl)sulfonyl]-3-ethoxycarbonylpiperazine hydrochloride (WO96/10022) (1.00 g) and benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP®) (1.50 g) were dissolved. Triethylamine (0.40 ml) was added to the resulting solution, followed by stirring overnight at room temperature. After the reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue. The resulting mixture was washed with water and saturated aqueous NaCl solution and then, dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (505 mg, 30%) was obtained.

後処理

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washThe resulting mixture was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (505 mg, 30%)
  8. customwas obtained

出典と根拠

ORDレコード
ord-93559d8da7be42c5ae2bb390dae84e41
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

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