2-Mesitylenesulfonyl chloride → 4-[[(2,4,6-trimethylphenyl)sulfonyl]amino]-L-phenylalanine

HRID 393439Notes

Reaction equation

HRID 393439 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C@@H:7]([C:26]([OH:28])=[O:27])[NH:8]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:4][CH:3]=1.[CH3:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[C:33]=1[S:40](Cl)(=[O:42])=[O:41]>N1C=CC=CC=1>[CH3:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[C:33]=1[S:40]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([C:26]([OH:28])=[O:27])[NH2:8])=[CH:29][CH:30]=1)(=[O:41])=[O:42]

Participants

4

Reactant 2

HCID 130462-Mesitylenesulfonyl chlorideHCID 7019927Fmoc-4-Amino-L-phenylalanine2×

Product 1

HCID 544513294-[[(2,4,6-trimethylphenyl)sulfonyl]amino]-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine on Wang resin (3.0 g, 2.28 mmol) obtained from Example 62 was suspended in pyridine (15 mL), the slurry was cooled to 0° C. and 2,4,6-trimethylphenylsulfonyl chloride (2.49 g, 11.4 mmol) was added. The resulting mixture was agitated for 2 hr. The mixture was filtered and washed with dichloromethane and methanol. The coupling procedure was repeated. The resulting resin was treated with 25% piperidine in N-methylpyrrolidinone (2×15 min) and was washed with dichloromethane and methanol to give 4-[[(2,4,6-trimethylphenyl)sulfonyl]amino]-L-phenylalanine on Wang resin.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane and methanol
  3. additionThe resulting resin was treated with 25% piperidine in N-methylpyrrolidinone (2×15 min)
  4. washwas washed with dichloromethane and methanol

Sources & evidence

ORD record
ord-e2ced661281447f3851978e4012af3a9
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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