L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 131720850, compound

HRID 2395141Notes

Reaction equation

HRID 2395141 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[S:12][C:13]1[C:14]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])=[C:15]([O:32][CH3:33])[CH:16]=[CH:17][C:18]=1[N:19]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[NH:45]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:46]([C:54](O)=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[C:60]([O:59][C:57]([NH:45][C@H:46]([C:54]([CH:9]([NH2:8])[C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[S:12][C:13]1[C:14]([CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:36])=[C:15]([O:32][CH3:33])[CH:16]=[CH:17][C:18]=1[N:19]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:58])([CH3:62])([CH3:63])[CH3:61]

Participants

3

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 131720849HCID 131720849, compound

Product 1

HCID 131720850HCID 131720850, compound

Procedure

72.8 mg of benzyl (6-aminomethyl-3,7-dimethoxy-10-hexylphenothiazin-4-yl)-acetate trifluoroacetate were reacted with 39.7 mg of Boc-Phe-OH analogously to that described in Example 4.7.1. The crystalline benzyl [6-((N-tert.-butoxycarbonyl-L-phenylalanyl)-aminomethyl)-10-hexyl-3,7-dimethoxyphenothiazin-4-yl]-acetate obtained was dissolved in trifluoroacetic acid, whereupon the solution was left to stand at 20° for 10 minutes and concentrated in a vacuum. The residue was dissolved in 3 ml of DMF, whereupon 84.3 mg of Z-Tyr(Bzl)-ONp were added and the pH value was adjusted to 8.5 with DIPEA. After 3 hours the reaction mixture was worked up as described in Example 4.7.1. The crystalline benzyl [6-(((N,O-bis-benzyloxycarbonyl-L-tyrosyl)-L-phenylalanyl)-aminomethyl)-10-hexyl-3,7-dimethoxy-phenothiazin-4-yl]-acetate obtained was further processed analogously to that described in Example 2.2.1., whereby the crude product was crystallized from ethanol. 21.3 mg of 10-hexyl-3,7-dimethoxy-4,6-cyclo-[acetyl-L-tyrosyl-L-phenylalanyl-aminomethyl]phenothiazine were obtained; MS: 723.5 MH+.

Sources & evidence

ORD record
ord-346fbb89ad9e406e845ed2afb4d285e8
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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