HCID 17865655, compound → HCID 69199050, compound

HRID 131105Notes

Reaction equation

HRID 131105 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([OH:17])=O.[NH2:18][C@H:19]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]1[CH2:39][CH2:38][O:37][CH:36]1[O:40][CH3:41])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22]>>[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([NH:18][C@H:19]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]1[CH2:39][CH2:38][O:37][CH:36]1[O:40][CH3:41])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17]

Participants

3

Reactant 2

HCID 17865655HCID 17865655, compoundHCID 69196920HCID 69196920, compound2×

Product 1

HCID 69199050HCID 69199050, compoundYield 72%

Procedure

The experimental protocol used is the same as that described for the synthesis of intermediate 1.1, starting with 10H-phenoxazine-2-carboxylic acid (J. Org. Chem. 1960, 25, 747-753) and L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide (intermediate 1.6). The condensation product is purified by chromatography on a silica column (eluent: heptane/ethyl acetate: 3/7). A yellow solid is obtained with a yield of 72%. Melting point: 178-179° C.

Workup

  1. customThe condensation product is purified by chromatography on a silica column (eluent: heptane/ethyl acetate: 3/7)
  2. customA yellow solid is obtained with a yield of 72%

Sources & evidence

ORD record
ord-83d4cad06bbf47f88a12dda05356e6f9
Source dataset
uspto-grants-2008_06
Patent number
US07384933B2

Reaction notes

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