1,2-Dichloroethane → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide

HRID 1945479ノート

反応式

HRID 1945479 の反応式
[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)=CC=5N=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.C([NH2:37])C1OC=CC=1.[CH2:38](Cl)[CH2:39]Cl.C1C=CC2N(O)N=NC=2C=1.C[CH2:53][N:54]([CH:58](C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[CH3:53][N:54]([CH3:58])[C:26]([C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][C:11]([C:1]45[CH2:8][CH:7]6[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]6)[CH2:10]4)[CH2:2]5)=[CH:12][CH:13]=3)=[N:37][C:38]=2[CH:39]=1)=[O:28]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 3438FurfurylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

生成物 1

HCID 249668972-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide収率 95.5%

試薬・触媒・溶媒 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenol溶媒

実験手順

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (30.1 mg, 0.08 mmol), furfuryl amine (11.0 mg, 0.12 mmol, 0.01 ml), EDC (21.7 mg, 0.12 mmol) and HOBt (15.4 mg, 0.12 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.12 mmol, 0.02 ml). After string 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 (n-Hexane:EtOAc:MeOH=6:3:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide as a white solid (32.9 mg, 90.9% yield).

後処理

  1. customAfter string at room temperature, the 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 (n-Hexane:EtOAc:MeOH=6:3:1)

出典と根拠

ORDレコード
ord-7ab7cd6ccbd24ca99f72be340fac1f4f
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

反応ノート

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