Phthalimide → HCID 178499351, compound

HRID 336036Notes

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-03f93dc2f1c645b5903dfb3be8429d75
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884030B2

Reaction notes

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