N-(Benzyloxycarbonyl)-D-tryptophan → CBZ-D-Trp-Lys(BOC)-OtBu

HRID 2121325Notes

Reaction equation

HRID 2121325 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:26][C@H:27]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].Cl.OC1C2N=NNC=2C=CC=1.Cl.CNC(N=C=NCC)CCNC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13]([NH:26][C@H:27]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

7

Reactant 4

HCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 1381988513288-57-8HCID 230638721,3-Dimethylaminopropyl-3-ethylcarbodiimide hydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 131724346CBZ-D-Trp-Lys(BOC)-OtBuYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 406 mg of CBZ-D-Trp-OH (1.2 mmol), 302 mg of Lys(BOC)-OtBu HCl (1.0 mmol), 202 mg of hydroxybenzotriazole (1.5 mmol) and 366 mg of 4-dimethylaminopyridine (3 mmol) in 60 mL of methylene chloride was added 448 mg (1.5 mmol) of 1,3dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (EDC). After stirring for 3 hours 100 mL more methylene chloride was added to the reaction, and it was washed four times with 25 mL portions of 0.1 N hydrochloric acid solution, twice with 25 mL of 50% saturated sodium bicarbonate solution, once with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield 590 mg (100%) of CBZ-D-Trp-Lys(BOC)-OtBu.

Workup

  1. additionwas added to the reaction, and it
  2. washwas washed four times with 25 mL portions of 0.1 N hydrochloric acid solution
  3. dry with materialtwice with 25 mL of 50% saturated sodium bicarbonate solution, once with 50 mL of saturated brine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2f2fa68bfd2742b7968a4caf121ee38d
Source dataset
uspto-grants-2004_02
Patent number
US06696418B1

Reaction notes

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