Phthalimide → HCID 178499351, compound

HRID 39295Notes

Reaction equation

O[C:2](C(F)(F)F)=O.[CH3:8][C:9]([CH3:36])([CH3:35])[C:10]#[C:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[C:14]([N:20]([C@@H:30]([CH3:34])[CH2:31][CH2:32]O)[C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([CH3:29])[CH2:25][CH2:24]2)=[O:22])[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:56]1(=[O:66])[NH:60][C:59](=[O:61])[C:58]2=[CH:62][CH:63]=[CH:64][CH:65]=[C:57]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:2][O:19][C:17]([C:15]1[S:16][C:12]([C:11]#[C:10][C:9]([CH3:36])([CH3:35])[CH3:8])=[CH:13][C:14]=1[N:20]([C@@H:30]([CH3:34])[CH2:31][CH2:32][N:60]1[C:56](=[O:66])[C:57]2[C:58](=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:59]1=[O:61])[C:21]([C@H:23]1[CH2:24][CH2:25][C@H:26]([CH3:29])[CH2:27][CH2:28]1)=[O:22])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 5-(3,3-dimethyl-but-1-ynyl)-3-[(3-hydroxy-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt (1.40 g, 3.23 mmol) in THF (30 mL) was cooled to 0° C. and triphenylphosphine (2.53 g, 9.69 mmol) was added followed by phthalimide (0.713 g, 4.84 mmol). The reaction was stirred until homogenious then DIAD (1.06 mL, 5.49 mmol) was added. After warming to rt., the reaction was determined to be complete by LC/MS in 1 h. The reaction was quenched with CH3OH (1.0 mL) and the solvent removed under reduced pressure. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[3-(1,3-dioxo-1,3-dihydro-isoindole-2-yl)-1-(S)-methyl propyl]-(trans-4-methyl-cyclohexylcarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (1.67 g, 92%) was isolated by silica gel chromatography as an off-white solid.

Workup

additionwas added
temperatureAfter warming to rt
customThe reaction was quenched with CH3OH (1.0 mL)
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-1e27753b2bd445c6b04d9f555973467d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524764B2

Reaction notes

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