Triethylamine → HCID 59184919, compound

HRID 1943323Notes

Reaction equation

HRID 1943323 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][O:41][C:42]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[O:43])=[CH:36][CH:35]=1)=[O:32])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:30])[NH2:29])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14].[OH:50][C@:51]1([C:92](O)=[O:93])[CH2:68][C@H:67]([O:69][C@@H:70]2[O:84][C@@H:83]([CH3:85])[C@H:73]3[O:74][C@H:75]4[N:80]([C@H:72]3[CH2:71]2)[CH2:79][CH2:78][O:77][C@@H:76]4[O:81][CH3:82])[C:66]2[C:53](=[C:54]([OH:91])[C:55]3[C:56](=[O:90])[C:57]4[C:62]([C:63](=[O:87])[C:64]=3[C:65]=2[OH:86])=[C:61]([O:88][CH3:89])[CH:60]=[CH:59][CH:58]=4)[CH2:52]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>ClCCl>[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:31]([NH:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:40][O:41][C:42]([N:44]2[CH2:45][CH2:46][N:47]([C:92]([C@@:51]3([OH:50])[CH2:68][C@H:67]([O:69][C@@H:70]4[O:84][C@@H:83]([CH3:85])[C@H:73]5[O:74][C@H:75]6[N:80]([C@H:72]5[CH2:71]4)[CH2:79][CH2:78][O:77][C@@H:76]6[O:81][CH3:82])[C:66]4[C:53](=[C:54]([OH:91])[C:55]5[C:56](=[O:90])[C:57]6[C:62]([C:63](=[O:87])[C:64]=5[C:65]=4[OH:86])=[C:61]([O:88][CH3:89])[CH:60]=[CH:59][CH:58]=6)[CH2:52]3)=[O:93])[CH2:48][CH2:49]2)=[O:43])=[CH:38][CH:39]=1)=[O:32])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:30])[NH2:29])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59184937HCID 59184937, compoundHCID 67121030HCID 67121030, compound

Product 1

HCID 59184919HCID 59184919, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 To the intermediate 60 (13.2 mg) a solution of crude (2S,4S)-2,5,12-trihydroxy-7-methoxy-4-{[(1S,3R,4aS,9S,9aR,10aS)-9-methoxy-1-methyloctahydro-1H-pyrano[4′,3′:4,5][1,3]oxazolo[2,3-c][1,4]oxazin-3-yl]oxy}-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-2-carboxylic acid 56 (9.3 mg) in anhydrous dichloromethane (2.6 ml), TBTU (5.3 mg, 0.0165 mmol), and anhydrous triethylamine (2.8 mg, 0.0275 mg) was added. The reaction mixture was stirred at room temperature under argon atmosphere for 15 minutes, until disappearance of the starting material (HPLC-MS analysis). The solvent was then evaporated under vacuum and the crude was purified by flash column chromatography (EtOH:AcOEt=1.5:8.5) on silica gel (230-400 mesh), affording 4.8 mg (red solid, yield calculated on PNU-159682=34%) of 55. MS (ESI): 1295 [M+H]+. Retention time=5.51 min(method 1).

Workup

  1. customThe solvent was then evaporated under vacuum
  2. customthe crude was purified by flash column chromatography (EtOH:AcOEt=1.5:8.5) on silica gel (230-400 mesh)
  3. customaffording

Sources & evidence

ORD record
ord-397a2658bc50464f82b8705d9c9303fe
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

Loading…