Dimethylformamide → 3-({4-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]phenyl}formamido)propanoic acid

HRID 1633884Notes

Reaction equation

HRID 1633884 reaction equation
[C:1]([NH:18][CH2:19]CC(O)=O)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C1C2C(N(CC3C=C[C:52]([C:53]([OH:55])=[O:54])=[CH:51]C=3)C(OC)=O)C3C(=CC=CC=3)C=2C=CC=1.F[P-](F)(F)(F)(F)F.Br[P+](N1[CH2:81][CH2:80]CC1)(N1CCCC1)N1CCCC1.CN(C=[O:86])C>C(N(CC)C(C)C)C>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1]([NH:18][CH2:19][C:25]3[CH:81]=[CH:80][C:28]([C:29]([NH:24][CH2:51][CH2:52][C:53]([OH:55])=[O:54])=[O:86])=[CH:27][CH:26]=3)=[O:2])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide3×HCID 8082PiperidineHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanineHCID 2733179PyBroPHCID 674838124-[(9H-fluoren-9-yl-methoxycarbonylamino)methyl]benzoic acid

Product 1

HCID 225021983-({4-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]phenyl}formamido)propanoic acid

Reagents, catalysts & solvents 1

HCID 521913N,N-Diethyl-2-propanamineSolvent

Procedure

To the above resin bound Fmoc β-alanine was added 500 μL of a 20% solution of piperidine in DMF. Upon shaking 30 min, the resin was drained and washed with 1 mL DMF containing 1-hydroxybenzotriazole (50 mg/mL) and DMF (2×1 mL). Then 200 μmol 4-[(9H-fluoren-9-yl-methoxycarbonylamino)methyl]benzoic acid (74.2 mg) dissolved in a mixture of 430 μL DMF and 70 μL diethylisopropylamine was added followed by 200 μmol bromo-tris-pyrrolidinophosphonium hexafluorophosphate (PyBrOP, 93 mg) dissolved in 500 μL DMF. The mixture was shaken for 4 hours at 25° C. followed by filtration and washing of the resin with 3×1 mL DMF.

Workup

  1. washwashed with 1 mL DMF
  2. additioncontaining 1-hydroxybenzotriazole (50 mg/mL) and DMF (2×1 mL)
  3. additionwas added
  4. stirringThe mixture was shaken for 4 hours at 25° C.
  5. filtrationfollowed by filtration
  6. washwashing of the resin with 3×1 mL DMF

Sources & evidence

ORD record
ord-98831ac4c99f41409baa9aea4ac6052a
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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