Tetrahydrofuran → HCID 59479668, compound

HRID 76320Notes

Reaction equation

HRID 76320 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[CH3:8])=[O:5])[CH3:3].[NH2:24][CH2:25][CH2:26][CH2:27][OH:28].C1COCC1>CN(C=O)C>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([NH:11][C@H:12]([C:14]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:16])[CH3:13])=[O:10])[CH3:8])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 90863-Amino-1-propanolHCID 14655139N-(tert-Butoxycarbonyl)-L-alanyl-L-alanyl-L-alanine

Product 1

HCID 59479668HCID 59479668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired compound was synthesized by the procedure of Example 4 using Boc-Ala-Ala-Ala-OH and H2N—(CH2)3—OH except that the solvent was a mixture of THF and DMF (8 h). In a typical reaction of 4.59 mmol scale, the desired product was obtained in good yields, (1.401 gm, 79%) as a solid (m.p.—201° C.) after purification by silica gel flash column chromatography (MeOH:EtOAc—1:25). TLC (MeOH:DCM—1: 3; Rf—0.53).

Workup

  1. customIn a typical reaction of 4.59 mmol scale

Sources & evidence

ORD record
ord-e41413ddacd74e8ebbc62b50b7eb61c9
Source dataset
uspto-grants-2014_09
Patent number
US08835602B2

Reaction notes

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