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

HRID 2094702Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

washAfter the acylation step, the resin was washed with THF
washThe resin was washed with DCM
customisolated
custompurified as

Sources & evidence

ORD record: ord-7dda6970aaf34587a61dcda752811e9b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445530B2

Reaction notes

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