1,2-Dichloroethane → Fmoc-Indanylglycine Val-OAllyl

HRID 1631426Notes

Reaction equation

HRID 1631426 reaction equation
[C:1]([N:18]([CH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][C:20]([OH:22])=[O:21])([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].CN([CH:35]=[O:36])C.C[N:38]1[CH2:43][CH2:42][O:41]CC1.[CH2:44](Cl)[CH2:45]Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([N:18]([CH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][C:20]([OH:22])=[O:21])([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].[NH2:38][C@H:43]([C:42]([O:36][CH2:35][CH:44]=[CH2:45])=[O:41])[CH:5]([CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 68451954Fmoc indanylglycine

Product 1

HCID 131731716Fmoc-Indanylglycine Val-OAllyl

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Fmoc Indanylglycine (0.54 g, 1.315 mmol) was solvated in CH2Cl2 (5 mL) and DMF (1.8 mL) followed with the addition of L-Val allylester (0.437 g, 1 eq), 4-methylmorpholine (0.15 ml, 1.04 eq) and 4 min latter DMAP (14.5 mg, 0.09 eq) then EDC (0.265 g, 1.05 eq). The mixture was stirred for 1 hour 45 min. Then it was extracted using EtOAc/brine. The organic layer was dried over MgSO4, filtered off and concentrated to dryness.

Workup

  1. extractionThen it was extracted
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered off
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cd884ca664c64ec3908841bf39ff7458
Source dataset
uspto-grants-2014_07
Patent number
US08791235B2

Reaction notes

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