Water → HCID 178427516, compound

HRID 2384950Notes

Reaction equation

HRID 2384950 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.[NH2:63][C@H:64]([C:90]([C:92]([CH3:95])([CH3:94])[CH3:93])=[O:91])[CH2:65][CH2:66][CH2:67][NH:68][C:69](=[NH:89])[NH:70][S:71]([C:74]1[C:87]([CH3:88])=[C:85]([CH3:86])[C:84]2[O:83][C:80]([CH3:82])([CH3:81])[CH2:79][CH2:78][C:77]=2[C:75]=1[CH3:76])(=[O:73])=[O:72].C(=O)(O)[O-].[Na+]>ClCCl>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:63][C@H:64]([C:90]([C:92]([CH3:95])([CH3:94])[CH3:93])=[O:91])[CH2:65][CH2:66][CH2:67][NH:68][C:69](=[NH:89])[NH:70][S:71]([C:74]1[C:87]([CH3:88])=[C:85]([CH3:86])[C:84]2[O:83][C:80]([CH3:81])([CH3:82])[CH2:79][CH2:78][C:77]=2[C:75]=1[CH3:76])(=[O:72])=[O:73])=[O:5]

Participants

9

Reactant 7

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178427508HCID 178427508, compound

Product 1

HCID 178427516HCID 178427516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of commercially available Z-Pro-OH (3.9 g, 11.0 mmol) was dissolved in dry dichloromethane (25 ml) and cooled in an ice bath. HBTU (4.2 g, 11.0 mmol) was added followed by HOBt.H2O (1.68 g, 11.0 mmol) and DIEA (3.12 g, 24.2 mmol). The reaction mixture was stirred for 10 min and then to the above activated acid, H-Arg(Pmc)-t-Bu (5.0 g, 10.0 mmol) was added as a solid. The solution was allowed to come to RT and stirred for 20 h at RT. The mixture was poured into saturated sodium bicarbonate solution (100 mL) and stirred for 5 min. The organic layer was separated and washed with water (2×100 mL) and dried (sodium sulfate). Evaporation of the solvent yielded the product as colorless foam. Yield: 8.2 g (100%).

Workup

  1. temperaturecooled in an ice bath
  2. customto come to RT
  3. stirringstirred for 20 h at RT
  4. stirringstirred for 5 min
  5. customThe organic layer was separated
  6. washwashed with water (2×100 mL)
  7. dry with materialdried (sodium sulfate)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-af324a839c8043e3ac0359a22e44ab51
Source dataset
uspto-grants-2012_09
Patent number
US08263739B2

Reaction notes

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