4-Methylmorpholine → HCID 131719362, compound

HRID 2268693Notes

Reaction equation

HRID 2268693 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, 3.4 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-aa18c437dc754d1db74b04a08183971e
Source dataset
uspto-grants-2001_12
Patent number
US06328970B1

Reaction notes

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