Dicyclohexylcarbodiimide → HCID 89348460, compound

HRID 488528Notes

Reaction equation

HRID 488528 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([P:22]([CH2:29][SH:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:31]([NH:34][C@H:35]([C:43](O)=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:33])[CH3:32]>CN(C=O)C>[NH:34]([C:31]([CH3:32])=[O:33])[C@H:35]([C:43]([S:30][CH2:29][P:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 10868Dicyclohexylcarbodiimide2×HCID 74839N-Acetyl-L-phenylalanineHCID 11230015(DIPHENYLPHOSPHINO)METHANETHIOL

Product 1

HCID 89348460HCID 89348460, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method B (DCC coupling). Compound 20 (500 mg, 2.15 mmol) and N-acetylphenylalanine (446 mg, 2.15 mmol) were dissolved in DMF (15 mL) under Ar(g). 1,3-Dicyclohexylcarbodiimide (DCC; 489 mg, 2.37 mmol) was then added, and the reaction mixture was stirred for 12 h at room temperature. The 1,3-dicyclohexylurea (CU) by-product was removed by filtration, solvent was removed under reduced pressure, and the residue was purified by chromatography as in Method A. AcPheSCH2PPh2 was isolated as a white solid in 84% yield. Spectral data. 1H NMR (CDCl3, 300 MHz) δ 7.44-7.39 (m, 4 H), 7.35-7.33 (m, 6 H), 7.26-7.21 (m, 3 H), 7.11-7.09 (m, 2 H), 6.29 (d, J=8.4 Hz, 1 H), 4.98-4.91 (m, 1 H), 3.57-3.44 (m, 2 H), 3.09 (dd, J=14.1, 5.4 Hz, 1 H), 2.93 (dd, J=14.1, 7.5 Hz, 1 H), 1.88 (s, 3 H) ppm; 13C NMR (CDCl3, 125 MHz) δ 198.901, 169.86, 135.50, 132.62 (d, J=19.4 Hz), 129.11 (d, J-9.8 Hz) 128.79 (d, J=35.9 Hz), 128.50, 128.45, 126.99, 59.56, 37.99, 25.61 (d, J=24.4 Hz), 22.88 ppm; 31P NMR (CDCl3, 121 MHz −44.55 ppm.

Workup

  1. customThe 1,3-dicyclohexylurea (CU) by-product was removed by filtration, solvent
  2. customwas removed under reduced pressure
  3. customthe residue was purified by chromatography as in Method A

Sources & evidence

ORD record
ord-7a6139e3bcd74515b948b495637b920e
Source dataset
uspto-grants-2005_12
Patent number
US06972320B2

Reaction notes

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