Triphenylphosphine → 2-{3-[2-(3-Chloro-phenyl)-ethoxy]-4-methyl-benzoylamino}-indane-2-carboxylic acid

HRID 2405243ノート

反応式

HRID 2405243 の反応式
[NH2:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[OH:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18]([OH:20])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:44][C:45]1[CH:46]=[C:47]([CH2:51][CH2:52]O)[CH:48]=[CH:49][CH:50]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:44][C:45]1[CH:46]=[C:47]([CH2:51][CH2:52][O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:18]([NH:1][C:2]2([C:11]([OH:13])=[O:12])[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10]2)=[O:20])[CH:48]=[CH:49][CH:50]=1

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 685123-Hydroxy-4-methylbenzoic acidHCID 78856m-Chlorophenethylic alcoholHCID 2509362-Aminoindane-2-carboxylic acidHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 444824192-{3-[2-(3-Chloro-phenyl)-ethoxy]-4-methyl-benzoylamino}-indane-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

The synthesis was carried out on 0.15 g of PL Wang resin (1.7 mmol/g). The attachment of 2-amino-indane-2-carboxylic acid and the acylation with 3-hydroxy-4-methylbenzoic acid were performed as in described in example 173. After the acylation step, the resin was washed with THF and a solution of triphenylphosphine (10 equivalents) and 2-(3-chlorophenyl)-ethanol (10 equivalents) in THF was added to the resin. The slurry was cooled to 0° C., DIAD (10 equivalents) was added to the cooled mixture, and the reaction mixture was shaken overnight at room temperature. The resin was washed with DCM. The compound was cleaved, isolated and purified as in described in example 173. Yield: 2.3 mg.

後処理

  1. washAfter the acylation step, the resin was washed with THF
  2. washThe resin was washed with DCM
  3. customisolated
  4. custompurified as

出典と根拠

ORDレコード
ord-853ef9f2303241829010fa3c94b3e1ae
出典データセット
uspto-grants-2014_08
特許番号
US08802720B2

反応ノート

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