Dimethylformamide → HCID 131720846, compound

HRID 2395186Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]2[C:9]=1[S:10][C:11]1[C:12](CC(O)=O)=[C:13]([O:32][CH3:33])[CH:14]=[C:15]([CH2:30][NH2:31])[C:16]=1[N:17]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([NH:46][C@H:47]([C:49]([NH:51][CH2:52][C:53]([OH:55])=O)=[O:50])[CH3:48])=[O:45])=[O:41].[CH:56](Cl)(Cl)Cl.[CH3:60][OH:61].CN([CH:65]=[O:66])C>>[CH3:60][O:61][C:53](=[O:55])[CH2:52][NH:51][C:49](=[O:50])[C@H:47]([CH3:48])[NH:46][C:44](=[O:45])[CH2:43][NH:42][C:40](=[O:41])[CH2:39][N:38]([C:12]1[C:11]2[S:10][C:9]3[C:18](=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[C:8]=3[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[N:17]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:16]=2[C:15]([CH2:30][NH2:31])=[CH:14][C:13]=1[O:32][CH3:33])[C:65](=[O:66])[CH3:56]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7020061HCID 7020061, compound

HCID 21584188Chloroform methanol

HCID 131720847HCID 131720847, compound

Product 1

HCID 131720846HCID 131720846, compoundYield 77.6%

Procedure

A solution of 700 mg (1.31 mmol) of (6-tert.-butoxycarbonyl-aminomethyl-10-hexyl-3,7-dimethoxy-phenothiazin-4-yl)-acetic acid, 547 mg (1.44 mmol) of 1-benzotriazol-1-yl-N,N,N',N'-tetramethylnonium hexafluorophosphate (HBTU) and 488.1 mg (1.44 mmol) of Gly-Gly-Ala-Gly (SEQ ID NO:4)methyl ester hydrochloride in 5 ml of DMF was processed analogously to that described in Example 4.8.3., whereupon, after chromatography on silica gel with chloroform/methanol (9:1), 800 mg (77.6%) of (6-tert.-butoxycarbonyl-aminomethyl-10-hexyl-3,7-dimethoxy-phenothiazin-4-yl)-acetyl-glycyl-glycyl-L-alanyl-glycine methyl ester were obtained as an amorphous foam.

Sources & evidence

ORD record: ord-6477c6e87ade4f9aaa977dcfced6e060
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811548

Reaction notes

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