4-Methylmorpholine → HCID 131719362, compound

HRID 1264147Notes

Reaction equation

HRID 1264147 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].Cl.[C:18](OC(=O)CN)([CH3:21])([CH3:20])[CH3:19].C[N:28]1[CH2:33][CH2:32][O:31]CC1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[NH2:28][C@H:33]([C:32]([CH:4]([CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)[C:2](=[O:1])[OH:3])=[O:31])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 171548BiotinHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 131719362HCID 131719362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of biotin (0.83 g, 3A mmol) in 60 mL of DMF was added glycine t-butyl ester hydrochloride (0.57 g, 3.4 mmol), N-methylmorpholine (0.92 mL, 8.36 mmol), 1-hydroxybenzotriazole (0.61 g, 3.99 mmol) and 1-(3-Dimethylaminopropyl)-3-ethylcarbo-diimide hydrochloride (0.65 g, 3.4 mmol). The reaction mixture was stirred at room temperature for 7 days. The DMF was concentrated, ethyl acetate was added, and the organic layer was washed with water, 0.5'N HCl, saturated sodium bicarbonate, and brine. The ethyl acetate layer was dried (MgSO4) and concentrated to yield tert-butylglycylbiotin as a white solid which was primarily one spot on TLC (0.611 g, 1.71 mmol, 50%). Mass spec [M+H]+at m/z 358.

Workup

  1. concentrationThe DMF was concentrated
  2. additionethyl acetate was added
  3. washthe organic layer was washed with water, 0.5'N HCl, saturated sodium bicarbonate, and brine
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2fff1dd1f699489783b0c8b49777a4cc
Source dataset
uspto-grants-2003_04
Patent number
US06541612B2

Reaction notes

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