HCID 178427513, compound → HCID 178427510, compound

HRID 2384948Notes

Reaction equation

HRID 2384948 reaction equation
[N:1]1(C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)[CH2:47][CH2:46][CH2:45][C@H:2]1[C:3]([N:5]1[CH2:44][CH2:43][CH2:42][C@H:6]1[C:7]([NH:9][C@H:10]([C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])=[O:37])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:35])[NH:16][S:17]([C:20]1[C:33]([CH3:34])=[C:31]([CH3:32])[C:30]2[O:29][C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][C:23]=2[C:21]=1[CH3:22])(=[O:19])=[O:18])=[O:8])=[O:4]>N1CCCCC1.C(#N)C>[NH:1]1[CH2:47][CH2:46][CH2:45][C@H:2]1[C:3]([N:5]1[CH2:44][CH2:43][CH2:42][C@H:6]1[C:7]([NH:9][C@H:10]([C:36]([C:38]([CH3:39])([CH3:40])[CH3:41])=[O:37])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:35])[NH:16][S:17]([C:20]1[C:33]([CH3:34])=[C:31]([CH3:32])[C:30]2[O:29][C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][C:23]=2[C:21]=1[CH3:22])(=[O:19])=[O:18])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 178427513HCID 178427513, compound

Product 1

HCID 178427510HCID 178427510, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8082PiperidineSolvent

Procedure

A solution of the Fmoc-Pro-Pro-Arg(Pmc)-t-Bu (4.15 g, 4.4 mmol) in 10% piperidine in acetonitrile (v/v, 50 mL) was stirred at RT for 30 min. All the volatiles were removed under reduced pressure and the residue was chromatographed on flash silica gel (360.0 g). All the fast moving impurities were removed by washing the column with 10% methanol in chloroform. Continued elution with 20% methanol in chloroform containing 0.1% TEA eluted the required amine. The fractions containing the amine were pooled and evaporated to furnish the amine as a colorless foam. Rf: 0.125 (20% methanol in chloroform). Yield: 3.0 g (98%). MS m/z 691.4 [M+H].

Workup

  1. customAll the volatiles were removed under reduced pressure
  2. customthe residue was chromatographed on flash silica gel (360.0 g)
  3. customwere removed
  4. washby washing the column with 10% methanol in chloroform
  5. washContinued elution with 20% methanol in chloroform containing 0.1% TEA
  6. washeluted the required amine
  7. additionThe fractions containing the amine
  8. customevaporated

Sources & evidence

ORD record
ord-50d2857d1f714c6fab2db55e50700834
Source dataset
uspto-grants-2012_09
Patent number
US08263739B2

Reaction notes

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