4-Aminobenzyl alcohol → HCID 131726473, compound

HRID 1354874Notes

Reaction equation

[NH:1]([C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])[C@@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:30]([OH:32])=[O:31])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].[CH3:39][C:40]([NH:51][CH2:52][CH:53]([OH:69])[CH2:54][O:55][C:56]1[C:61]2[C:62]3[C:67]([NH:68][C:60]=2[CH:59]=[CH:58][CH:57]=1)=[CH:66][CH:65]=[CH:64][CH:63]=3)([C:42]1[CH:47]=[CH:46][C:45]([N:48]=[N+:49]=[N-:50])=[CH:44][CH:43]=1)[CH3:41].[CH3:70][C:71]([NH:82][CH2:83][CH:84]([OH:100])[CH2:85][O:86][C:87]1[C:92]2[C:93]3[C:98]([NH:99][C:91]=2[CH:90]=[CH:89][CH:88]=1)=[CH:97][CH:96]=[CH:95][CH:94]=3)([C:73]1[CH:78]=[CH:77][C:76]([N:79]=[N+:80]=[N-:81])=[CH:75][CH:74]=1)[CH3:72].[NH2:101][C:102]1[CH:109]=[CH:108][C:105]([CH2:106][OH:107])=[CH:104][CH:103]=1.[OH:110]N1C2C=CC=CC=2N=N1>C(N(CC)C=O)C.CC(O)C.C(OCC)(=O)C>[NH:1]([C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])[C@@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:30]([OH:32])=[O:31])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[O:16])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:3].[CH3:41][C:40]([NH:51][CH2:52][CH:53]([OH:69])[CH2:54][O:55][C:56]1[C:61]2[C:62]3[C:67]([NH:68][C:60]=2[CH:59]=[CH:58][CH:57]=1)=[CH:66][CH:65]=[CH:64][CH:63]=3)([C:42]1[CH:47]=[CH:46][C:45]([N:48]=[N+:49]=[N-:50])=[CH:44][CH:43]=1)[CH3:39].[CH3:72][C:71]([NH:82][CH2:83][CH:84]([OH:100])[CH2:85][O:86][C:87]1[C:92]2[C:93]3[C:98]([NH:99][C:91]=2[CH:90]=[CH:89][CH:88]=1)=[CH:97][CH:96]=[CH:95][CH:94]=3)([C:73]1[CH:78]=[CH:77][C:76]([N:79]=[N+:80]=[N-:81])=[CH:75][CH:74]=1)[CH3:70].[CH:104]1[C:105]([C:106]([OH:110])=[O:107])=[CH:108][CH:109]=[C:102]([NH2:101])[CH:103]=1

Participants

Conditions

Temperature: -8 °C

Procedure

100 mg (0.105 mmol) of Aloc-D-Ala-Phe-Lys(Aloc)-PABC-PABC-PNP 18 was dissolved in dry N,N-diethylformamide under an argon atmosphere and cooled to −8° C. 4-Aminobenzylalcohol (14.2 mg, 1.1 equiv), dipea (18.3 μl, 1.0 equiv) and 1-hydroxybenzotriazole (HOBt) (4 mg, 0.3 equiv) were added. The reaction mixture was stirred for 48 hours at room temperature, and diluted with 10% 2-propanol/ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate, 0.5 N potassium bisulfate, and brine, dried over sodium sulfate (Na2SO4), and evaporated to yield the desired product 34 as a cream colored powder 86 mg (88%). 1H NMR (300 MHz CDCl3) δ 0.95–2.05 (m, 9H, 3CH2-Lys and CH3-Ala), 2.88–3.11 (m, 4H, 2H Bn-Phe and N—CH2-Lys), 3.95–4.62 (m, 7H, 3Hα and 4H Aloc), 4.75 (s, 2H, CH2—OH), 5.12–5.21 (m, 6H, 4 Aloc and CH2-Bn), 5.09 (s, 2H, CH2-Bn), 5.65–6.00 (m, 2H, Aloc), 6.79–7.41 (m, 15H, aromatic) 7.62 (d, 2H, aromatic) ppm; MS (FAB) m/e 959 (M+Na)+.

Workup

washThe organic layer was washed with water, saturated sodium bicarbonate, 0.5 N potassium bisulfate, and brine
dry with materialdried over sodium sulfate (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-6769265bac6a4d3282a6199f1951bc5d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223837B2

Reaction notes

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