N-Hydroxysuccinimide → N,N'-Bis-(9-Fluorenylmethyloxycarbonyl)-D-Lysyloxy Succinimide

HRID 1680211

Reaction equation

HRID 1680211 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:42]([OH:44])=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][CH:29]3[C:41]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:35]4[C:30]3=[CH:31][CH:32]=[CH:33][CH:34]=4)=[O:26])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O[N:46]1[C:50](=[O:51])[CH2:49][CH2:48][C:47]1=[O:52].Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C>C(OC(=O)C)C.CN(C)C=O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:42]([O:44][CH:48]3[CH2:49][C:50](=[O:51])[NH:46][C:47]3=[O:52])=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][CH:29]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=4[C:36]4[C:41]3=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:26])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22816294Fmoc-D-lys(fmoc)-OH

Product 1

HCID 22816295N,N'-Bis-(9-Fluorenylmethyloxycarbonyl)-D-Lysyloxy Succinimide

Reagents, catalysts & solvents 1

HCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

To a stirred solution of N,N'-bis-(9-fluorenylmethyloxycarbonyl)-D-lysine (12.0 g) in 360 ml of an ethylacetate:dimethylformamide (35:1) mixture are added N-hydroxysuccinimide (3.1 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) and diisopropylethylamine (2.0 ml). After 15 hours the solution is washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, and brine, dried over magnesium sulfate, and 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.

Workup

  1. washAfter 15 hours the solution is washed successively with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo to about 20 ml
  4. additionThe solution is added to hexane (1 l.)
  5. customthe precipitate is collected
  6. customdried

Sources & evidence

ORD record
ord-411aefadc51d4b08b86231303004d859
Source dataset
uspto-grants-1981_06
Patent number
US04272525

Linked notes

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