Dichloromethane → cis-4-Benzyloxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1271720ノート

反応式

HRID 1271720 の反応式
[C:1]([O:5][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]([NH2:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[S:31][C:30]([C:32](Cl)=[O:33])=[CH:29][CH:28]=1.CCN(CC)CC.C(Cl)Cl>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[C@H:10]([NH:25][C:32]([C:30]2[S:31][C:27]([Cl:26])=[CH:28][CH:29]=2)=[O:33])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 69440349tert-Butyl (3R,4S)-3-amino-4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

生成物 1

HCID 69443846cis-4-Benzyloxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester収率 37.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Cis-3-amino-4-benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester (450 mg, 1.288 mmol), from Part F of Example 112, was added to a cooled mixture (0° C.) of 5-chloro-thiophen-carboxylic chloride (233 mg, 1.288 mmol), Et3N (0.54 mL, 3.864 mmol), and CH2Cl2 (10 mL). The mixture stirred overnight at rt. EtOAc (70 mL) was added. The mixture was washed with brine, and the organic phase dried over MgSO4 and concentrated. The crude product was purified by silica gel flash column chromatography (30% MeOH/EtOAc) to yield cis-4-benzyloxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (236 mg). LC-MS: (M-100): 394.

後処理

  1. washThe mixture was washed with brine
  2. dry with materialthe organic phase dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash column chromatography (30% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-ef6f8e86175043079530f03e055d0089
出典データセット
uspto-grants-2007_04
特許番号
US07205318B2

反応ノート

読み込み中…