Dimethylformamide → HCID 131730293, compound

HRID 1944837Notes

Reaction equation

HRID 1944837 reaction equation
[C:1]([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ON1C(=O)CCC1=O.CN(C=O)C.[NH2:37][CH:38]([CH2:41][OH:42])[CH2:39][OH:40]>ClCCl.N1C=CC=CC=1>[NH:18]([C:1]([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2])[CH2:19][CH2:20][C:21]([OH:23])=[O:22].[NH2:37][CH:38]([CH2:41][OH:42])[CH2:39][OH:40]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 68294SerinolHCID 80170N-HydroxysuccinimideHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanine

Product 1

HCID 131730293HCID 131730293, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Fmoc-β-alanine (84.5 g, 271 mmol) and N-hydroxysuccinimide (31.2 g, 271 mmol) are dissolved in dichloromethane (850 mL) and DMF (43 mL) with magnetic stirring. N,N-dicyclohexylcarbodiimide (56.0 g, 271 mmol) dissolved in dichloromethane (100 mL) is added in one portion. After stirring 1.5 hours at room temperature, the reaction mixture was filtered, and transferred to a mixture of serinol (24.7 g, 271 mmol) in pyridine (380 mL) and allowed to react 16 hours overnight. The mixture is evaporated to a semi-solid residue, and co-evaporated 3×400 mL toluene to remove the remaining pyridine. The solid residue is refluxed in dichloromethane (3.0 L) and stored at −20° C. for 2 hours. The product was collect by filtration in a sintered glass funnel, and washed 2×1000 mL dichloromethane, and 1×1000 mL diethyl ether. Drying overnight under high vacuum yielded 92.8 g (89%) of 1.

Workup

  1. additionis added in one portion
  2. filtrationthe reaction mixture was filtered
  3. customto react 16 hours overnight
  4. customThe mixture is evaporated to a semi-solid residue
  5. customto remove the remaining pyridine
  6. temperatureThe solid residue is refluxed in dichloromethane (3.0 L)
  7. waitstored at −20° C. for 2 hours
  8. filtrationThe product was collect by filtration in a sintered glass funnel
  9. washwashed 2×1000 mL dichloromethane, and 1×1000 mL diethyl ether
  10. customDrying overnight under high vacuum

Sources & evidence

ORD record
ord-4ee89ddfa74b45ecae058607c9cfcea0
Source dataset
uspto-grants-2013_03
Patent number
US08394948B2

Reaction notes

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