Triethylamine → Unii-118E4WJ2X6

HRID 74826Notes

Reaction equation

HRID 74826 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]([N:15]([CH3:22])[C:16]([CH3:21])([C:18]([OH:20])=O)[CH3:17])=[O:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:54][O:55][C@@H:56]([C@@H:73]1[CH2:77][CH2:76][CH2:75][N:74]1[C:78](=[O:97])[CH2:79][C@@H:80]([O:95][CH3:96])[C@@H:81]([N:86]([CH3:94])[C:87](=[O:93])[C@H:88]([CH:90]([CH3:92])[CH3:91])[NH2:89])[C@@H:82]([CH3:85])[CH2:83][CH3:84])[C@@H:57]([CH3:72])[C:58]([NH:60][C@H:61]([C:69]([OH:71])=[O:70])[CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:59]>ClCCl>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]([CH3:22])[C:16]([CH3:17])([C:18]([NH:89][C@H:88]([C:87]([N:86]([C@@H:81]([C@@H:82]([CH3:85])[CH2:83][CH3:84])[C@H:80]([O:95][CH3:96])[CH2:79][C:78]([N:74]1[CH2:75][CH2:76][CH2:77][C@H:73]1[C@H:56]([O:55][CH3:54])[C@@H:57]([CH3:72])[C:58]([NH:60][C@H:61]([C:69]([OH:71])=[O:70])[CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:59])=[O:97])[CH3:94])=[O:93])[CH:90]([CH3:91])[CH3:92])=[O:20])[CH3:21])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86685780N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N,2-dimethylalanineHCID 86685781N-{(2R,3R)-3-methoxy-3-[(2S)-1-{(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]-L-phenylalanine

Product 1

HCID 86685783Unii-118E4WJ2X6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of #249 (382 mg, 1.23 mM) in 5 mL of dichloromethane, HATU (482 mg, 1.23 mM) was added followed by triethylamine (0.52 mL, 1.23 mM). The reaction was allowed to stir for 1 hour at room temperature followed by the addition of #250 (762 mg, 1.23 mM). The reaction was allowed to stir for 3 hours. Reaction was concentrated in vacuo. Reverse phase purification (MethodL) followed by lyophilization yielded a white solid mc#120 (124 mg, 11%). HPLC (Protocol A at 45° C.;) m/z 911.5 [M+H+], retention time=9.676 minutes.

Workup

  1. stirringto stir for 3 hours
  2. customReaction
  3. concentrationwas concentrated in vacuo
  4. customReverse phase purification (MethodL)
  5. customyielded a white solid mc#120 (124 mg, 11%)
  6. customat 45° C.

Sources & evidence

ORD record
ord-d805b92339204ddca040bd99df5d7862
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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