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Phthalimide → HCID 178499351, compound

HRID 39295
Notes
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Reaction equation

HRID 39295 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178461722HCID 178461722, compound

Product 1

HCID 178499351HCID 178499351, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. additionwas added
  2. temperatureAfter warming to rt
  3. customThe reaction was quenched with CH3OH (1.0 mL)
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes