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Ammonium Chloride → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide

HRID 1945477
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반응식

HRID 1945477 반응식
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23]([C:26]([OH:28])=O)=[CH:22][C:20]=5[N:21]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Cl-].[NH4+].C[N:34](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23]([C:26]([NH2:34])=[O:28])=[CH:22][C:20]=5[N:21]=4)=[CH:29][CH:30]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

생성물 1

HCID 249668962-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide
수율 4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (72.1 mg, 0.18 mmol), ammonium chloride (19.1 mg, 0.36 mmol) in DMF 4.0 mL was added HBTU (136.53 mg, 0.36 mmol) and DIPEA (0.063 ml, 0.36 mmol). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=15:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide as a yellow solid (2.7 mg, 4% yield).

후처리

  1. customthe mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=15:1)

출처 및 근거

ORD 기록
ord-961e7442b765492fb8d789a3cc642d17
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394799B2

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