Lysine hydrochloride, D- → Fmoc-D-lys(fmoc)-OH

HRID 1680210

Reaction equation

HRID 1680210 reaction equation
Cl.[NH2:2][C@@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].N([C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[N+]=[N-]>C(=O)([O-])[O-].[Na+].[Na+].CC(C)=O.O>[CH:30]1[C:31]2[CH:19]([CH2:18][O:17][C:15]([NH:2][C@@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:15]([O:17][CH2:18][CH:19]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]4[C:31]3=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:16])=[O:16])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 81691Lysine hydrochloride, D-HCID 13876407(9H-Fluoren-9-yl)methyl carbonazidate

Product 1

HCID 22816294Fmoc-D-lys(fmoc)-OH

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of D-lysine hydrochloride (4.5 g) in 175 ml of a sodium carbonate solution (10% in water):acetone (6:1) solution is added dropwise a solution of 9-fluorenylmethyl azidoformate in acetone (150 ml). After 16 hours the mixture is diluted with water and washed three times with hexane. The mixture is then acidified with concentrated hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate solution is washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, and brine, dried over magnesium sulfate, then concentrated in vacuo to about 20 ml. The solution is added to hexane (1 l.) and the precipitate is collected and dried to afford the title compound: NMR (dimethylsulfoxide) δ1.0-1.9 (m, 6H), 2.7-3.2 (m,2H), 3.8-4.7 (m,7H), 6.8-8.3 (m,19H).

Workup

  1. washwashed three times with hexane
  2. extractionextracted three times with ethyl acetate
  3. washThe ethyl acetate solution is washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to about 20 ml
  6. additionThe solution is added to hexane (1 l.)
  7. customthe precipitate is collected
  8. customdried

Sources & evidence

ORD record
ord-759176ab75af438bbfc15b21f31b707b
Source dataset
uspto-grants-1981_06
Patent number
US04272525

Linked notes

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