L-Aspartic Acid → Monascorubramin

HRID 981582Notes

Reaction equation

HRID 981582 reaction equation
[NH:1]([C:10]([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[C@H:2]([C:7](O)=O)CC(=O)O.CO[C:29]1C=CC(CC[NH-])=C[CH:30]=1.C1(N=C=NC2CCCCC2)CCCCC1.N[C@H:54]([C:59](O)=O)[CH2:55][C:56](=[O:58])[OH:57]>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:10]([NH:1][CH2:2][CH2:7][CH2:29][CH2:30][CH2:59][CH2:54][CH2:55][C:56]([OH:57])=[O:58])([O:12][CH2:13][CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[C:26]1=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:11]

Participants

6

Reactant 3

HCID 5960L-Aspartic AcidHCID 10868DicyclohexylcarbodiimideHCID 131716190HCID 131716190, compound

Product 1

HCID 2756091Monascorubramin

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Fmoc-Asp-2-(4-methoxyphenyl)ethyl amide from B (8 mmoles) was coupled with Sasrin resin (7 g; 0.7 mmole OH/g resin) in N,N-dimethylformamide (DMF) (50 ml) with dicyclohexylcarbodiimide (8 mmoles) and 4-dimethylamino-pyridine (0.5 g). The reaction was carried out overnight after which the resin was washed with DMF (5 x 40 ml) and CH2Cl2 (2 x 20 ml). The substitution was found to be 0.326 mmole Asp/g resin by amino acid analysis.

Workup

  1. washafter which the resin was washed with DMF (5 x 40 ml) and CH2Cl2 (2 x 20 ml)

Sources & evidence

ORD record
ord-de6f058134c44af0ba775415c60a89c0
Source dataset
uspto-grants-1991_02
Patent number
US04992463

Reaction notes

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