Formaldehyde → HCID 69444662、化合物

HRID 1271715ノート

反応式

HRID 1271715 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([NH:25][C:26](=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]3=[O:39])=[CH:29][CH:28]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C=O.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O.O.CC#N.CC(O)=O.CO>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][C@H:10]1[NH:25][C:26](=[O:40])[C:27]1[CH:28]=[CH:29][C:30]([N:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]2=[O:39])=[CH:31][CH:32]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

10

反応物 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 69437112Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 69444662HCID 69444662、化合物収率 54.3%

試薬・触媒・溶媒 5

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

Cis-4-Benzyloxycarbonylamino-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (285 mg, 0.52 mmol) was stirred in TFA (3 mL) and CH2Cl2 (5 mL) at rt for 1.5 h. LC/MS showed completion of the reaction (447.33 (M+H), tR=2.23 min, 10–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run). The solvents were evaporated. Half of the residue (0.26 mmol) was dissolved in CH3CN (2 mL). HCHO (37% wt in H2O, 0.20 mL) was added, followed by the addition of NaCNBH3 (78 mg). The resulting mixture was stirred at rt for 40 min. HOAc was added dropwise to neutralize the mixture. The resulting mixture was stirred for additional 1 h, extracted with EtOAc (3×), dried over MgSO4, filtered, and concentrated to dryness to give crude cis-{1-methyl-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester (130 mg). Anal. LC/MS (ESI) 461.14 (M+H), tR=2.63 min (10%–90% MeOH in H2O with 10 mM NH4OAc in a 4-min run).

後処理

  1. customThe solvents were evaporated
  2. stirringThe resulting mixture was stirred for additional 1 h
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-63bca03985634e86b73940c0c028287c
出典データセット
uspto-grants-2007_04
特許番号
US07205318B2

反応ノート

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