10H-Phenothiazine-2-carboxylic acid → HCID 11342902, compound

HRID 131099Notes

Reaction equation

HRID 131099 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S: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]([C:40]([NH:42][C@H:43]1[CH2:47][CH2:46][O:45][CH:44]1[O:48][CH3:49])=[O:41])[CH2:36][CH:37]([CH3:39])[CH3:38])=[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)[S: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]([C:40]([NH:42][C@H:43]1[CH2:47][CH2:46][O:45][CH:44]1[O:48][CH3:49])=[O:41])[CH2:36][CH:37]([CH3:38])[CH3:39])=[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 2271159310H-Phenothiazine-2-carboxylic acid2×HCID 69118046HCID 69118046, compound2×

Product 1

HCID 11342902HCID 11342902, compoundYield 21%

Procedure

The experimental protocol of this peptide condensation is the same as that described for the synthesis of intermediate 1.1, this time using 10H-phenothiazine-2-carboxylic acid (intermediate 1.10) and L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide (intermediate 1.8). The reaction product is purified by chromatography on silica (eluent: ethyl acetate/heptane in proportions of 7/3 to 1/1). 228 mg of a yellow solid is obtained with a yield of 21%. Melting point: 164-165° C.

Workup

  1. customThe reaction product is purified by chromatography on silica (eluent: ethyl acetate/heptane in proportions of 7/3 to 1/1)

Sources & evidence

ORD record
ord-152e200e3f76433e945e2f5c76c215f4
Source dataset
uspto-grants-2008_06
Patent number
US07384933B2

Reaction notes

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