Triethylamine → Boc-Arg(NO2)-Gly-NH2

HRID 261765Notes

Reaction equation

HRID 261765 reaction equation
[C:1]([N:8]([N+]([O-])=O)[C@H:9]([C:17]([OH:19])=O)[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:16])[NH2:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:24][CH2:25][C:26]([NH2:28])=[O:27].C(N(CC)CC)C.[OH2:36].[OH:37][N:38]1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(#N)C.O.O1CCCC1.C(#N)C>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([C:17]([NH:24][CH2:25][C:26]([NH2:28])=[O:27])=[O:19])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:16])[NH:15][N+:38]([O-:37])=[O:36]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723639Glycinamide hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178454196HCID 178454196, compound

Product 1

HCID 178454199Boc-Arg(NO2)-Gly-NH2Yield 71%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

This process is adapted from R. L. Huguenin et al., Helv. Chim. Acta, 48, 1885 (1965). Boc-nitroarginine (7.12 g., 22.3 mmole), glycinamide hydrochloride (2.46 g., 22.3 mmole), triethylamine (3.0 ml., 22.3 mmole) and 1-hydroxybenzotriazole monohydrate (3.42 g., 22.3 mmole) were dissolved in a mixture of tetrahydrofuran (THF) (30 ml.), acetonitrile (30 ml.), and water (8 ml.). Dicyclohexylcarbodiimide (4.66 g., 22.6 mmole) in 10 ml. of 1:1 THF/acetonitrile was added dropwise during 10 min. The resulting mixture was stirred at room temperature for 17 hours, filtered, and the solid washed with 1:1 THF/acetonitrile. Most of the product was mixed with dicyclohexyl urea in the filtered solids. Crystallization from MeOH/ether gave pure Boc-Arg(NO2)-Gly-NH2, 5.95 g. (71% yield): mp 151°-153° C. (dec); [α]58924 +0.21, [α]46324 +3.00 (c, 1.4, MeOH).

Workup

  1. filtrationfiltered
  2. washthe solid washed with 1:1 THF/acetonitrile
  3. additionMost of the product was mixed with dicyclohexyl urea in the filtered solids
  4. customCrystallization from MeOH/ether

Sources & evidence

ORD record
ord-cd88df05c5364d8a8948829c25523f19
Source dataset
uspto-grants-1979_05
Patent number
US04152322

Reaction notes

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