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

HRID 2094702노트

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HRID 2094702 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7dda6970aaf34587a61dcda752811e9b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445530B2

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