Diisopropylethylamine → HCID 23554371, compound

HRID 1859846Notes

Reaction equation

HRID 1859846 reaction equation
C1C=[C:5]2N=N[N:9](O)[C:4]2=[CH:3]C=1.[OH2:11].C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.[NH2:33][CH:34]1[N:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[C:38]2[CH:47]=[CH:48][CH:49]=[CH:50][C:37]=2[N:36]([CH2:51][C:52](=[O:57])[C:53]([CH3:56])([CH3:55])[CH3:54])[C:35]1=[O:58]>C(Cl)Cl>[NH2:9][C@H:4]([C:3]([NH:33][CH:34]1[N:40]=[C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[C:38]2[CH:47]=[CH:48][CH:49]=[CH:50][C:37]=2[N:36]([CH2:51][C:52](=[O:57])[C:53]([CH3:54])([CH3:55])[CH3:56])[C:35]1=[O:58])=[O:11])[CH3:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10498048(3RS)-Amino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one

Product 1

HCID 23554371HCID 23554371, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of L-Boc-alanine (1.57 g, 8.33 mmol), HOBt monohydrate (1.13 g, 8.33 mmol), diisopropylethylamine (1.45 mL, 8.33 mmol) and CH2Cl2 (40 mL) was purged with nitrogen and cooled in an ice bath. To the cold solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (1.60 g, 8.33 mmol) followed by a solution of 3-amino-2,3-dihydro-1-(3,3-dimethyl-2-oxobutyl)-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (2.92 g, 8.33 mmol) dissolved in CH2Cl2 (25 mL). The cold bath was removed and the solution stirred overnight at room temperature. The reaction mixture was extracted with H2O, 0.1 N aq. citric acid, 5% aq. NaHCO3, and brine. The remaining CH2Cl2 solution was dried (MgSO4) and concentrated to a yellow foam. The title compound was isolated via column chromatography (20% EtOAc/hexanes to 60% EtOAc/hexanes) to give 4.19 g (96% yield) of light yellow foam.

Workup

  1. temperaturecooled in an ice bath
  2. customThe cold bath was removed
  3. extractionThe reaction mixture was extracted with H2O, 0.1 N aq. citric acid, 5% aq. NaHCO3, and brine
  4. dry with materialThe remaining CH2Cl2 solution was dried (MgSO4)
  5. concentrationconcentrated to a yellow foam

Sources & evidence

ORD record
ord-1eb41cc1b9f8470b83967dcbd27b32b3
Source dataset
uspto-grants-2003_03
Patent number
US06528505B1

Reaction notes

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