L-Aspartic Acid → HCID 53241120, compound

HRID 1035324Notes

Reaction equation

HRID 1035324 reaction equation
[NH2:1][C@H:2]([C:7](O)=O)[CH2:3][C:4](O)=[O:5].[NH2:10][C@@H:11]([C:16](O)=O)[CH2:12]C(O)=O.C(N[C@H](C)C(OC)=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OC(=O)CNCC1C=CC=CC=1)C>>[CH3:12][C@@H:11]1[CH2:16][N:1]2[C@@H:2]([CH2:3][CH2:4][O:5][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=32)[CH2:7][NH:10]1

Participants

5

Reactant 4

HCID 5960L-Aspartic AcidHCID 80908N-Benzylglycine ethyl esterHCID 83887D-Aspartic AcidHCID 10987118methyl (2R)-2-(benzylamino)propanoate

Product 1

HCID 53241120HCID 53241120, compound

Procedure

The title compound was prepared according to the procedure outlined in Example 255 substituting L-aspartic acid for D-aspartic acid and (R)-methyl 2-(benzylamino)propanoate for N-benzylglycine ethyl ester. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.84-7.01 (m, 3H), 6.73-6.85 (m, 1H), 4.35-4.51 (m, 1H), 3.99-4.14 (m, 1H), 2.80-3.28 (m, 6H), 1.95-2.14 (m, 1H), 1.66-1.85 (m, 1H), 1.20 (d, J=6.44 Hz, 3H); MS (DCI) m/z 219 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customPurification via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-6276ac8ee3d14d18a3f609d416f66510
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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