Diisopropylethylamine → HCID 131720848, compound

HRID 2395140Notes

Reaction equation

HRID 2395140 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[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](CC(OCC3C=CC=CC=3)=O)=[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:56]([O:58][CH2:59][CH:60]1[C:72]2[C:67](=[CH:68][CH:69]=[CH:70][CH:71]=2)[C:66]2[C:61]1=[CH:62][CH:63]=[CH:64][CH:65]=2)=[O:57])[C@H:46]([C:53]([OH:55])=O)[CH2:47][O:48][C:49]([CH3:52])([CH3:51])[CH3:50].CN(C(ON1N=N[C:83]2[CH:84]=[CH:85][CH:86]=[CH:87][C:82]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:95]CN(C(C)C)C(C)C>>[CH:71]1[C:72]2[CH:60]([CH2:59][O:58][C:56]([NH:45][C@H:46]([C:53]([CH:9]([NH2:8])[C:10]3[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]4[C:11]=3[S:12][C:13]3[C:14]([CH2:2][C:3]([O:5][CH2:95][C:82]5[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=5)=[O:4])=[C:15]([O:32][CH3:33])[CH:16]=[CH:17][C:18]=3[N:19]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:55])[CH2:47][O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:57])[C:61]3[C:66](=[CH:65][CH:64]=[CH:63][CH:62]=3)[C:67]=2[CH:68]=[CH:69][CH:70]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131720849HCID 131720849, compound

Product 1

HCID 131720848HCID 131720848, compound

Procedure

250 mg of benzyl (6-aminomethyl-3,7-dimethoxy-10-hexyl-phenothiazin-4-yl)-acetate trifluoroacetate (1:1) were reacted with 153 mg of Fmoc-Ser(But)-OH, 141 mg of TBTU and 0.15 ml of DIPEA analogously to that described in Example 4.7.1. 20 mg of benzyl [6-((N-(9H-fluoren-9-ylmethoxycarbonyl)-O-tert.-butyl-L-seryl)-aminomethyl)-10-hexyl-3,7-dimethoxyphenothiazin-4-yl]-acetate were obtained; MS: 886.6 MH⊕.

Sources & evidence

ORD record
ord-5d08d8ec11b843b9996acb282ef36804
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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