Dimethylformamide → Ninhydrin

HRID 2422381Notes

Reaction equation

HRID 2422381 reaction equation
CC(OC(C)(C)C)C(NC(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C:4](O)=[O:5].[CH:30]1[CH:35]=[C:34]2N=NN(O)[C:33]2=[CH:32][CH:31]=1.[OH2:40].CC(C)N=C=NC(C)C.CN([CH:53]=[O:54])C.CN([CH:58]=[O:59])C.C(Cl)Cl>C(Cl)Cl>[CH:30]1[CH:35]=[C:34]2[C:4]([C:53]([OH:54])([OH:40])[C:58](=[O:59])[C:33]2=[CH:32][CH:31]=1)=[O:5]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 308567271989-35-0HCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 10236Ninhydrin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-α-Fmoc-N-im-trityl-L-histidine or N-α-Fmoc-O-t-butyl-L-serine (0.9282 g, 1.50 mmol) and HOBt monohydrate (0.2296 g, 1.50 mmol) in DMF/DCM (1:1) (10 ml) and DIC (0.1995 g, 1.58 mmol) was added to the deprotected resin. After 90 min., the peptide-resin was washed with DMF and DCM (both 4×12 mL×1 min.) and gave a negative Kaiser ninhydrin test. After removal of the Fmoc group as described, N-α-Fmoc-O-t-butyl-L-threonine (0.6006 g, 1.51 mmol) was coupled as described in the previous step, followed by removal of the Fmoc group. Coupling of N-α-Fmoc-α-methyl-2-fluoro-L-phenylalanine (0.4167 g, 0.993 mmol) was performed by mixing a solution of the amino acid and HOBt monohydrate (0.1529 g, 0.998 mmol) in DMF/DCM 1:1 (10 ml) and DIC (0.1260 g, 0.998 mmol) with the deprotected peptidyl-resin for 4 hours. After DMF and DCM (both 4×12 mL×1 min.) washes, a sample of the peptide-resin gave a negative Kaiser ninhydrin test. Performed steps 1 to 4 above to remove the Fmoc group.

Workup

  1. customAfter removal of the Fmoc group
  2. customfollowed by removal of the Fmoc group
  3. customboth 4×12 mL×1 min.

Sources & evidence

ORD record
ord-d7a39cbd147a482587bbd79508b7b057
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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