Diisopropylethylamine → (2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid

HRID 488643Notes

Reaction equation

HRID 488643 reaction equation
[C:1]([NH:4][CH:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]([C:46](=[O:54])[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([O:32][CH:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[C:19]([CH2:55][CH3:56])[CH:18]=1)[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](O)=[O:14])=[O:7])(=[O:3])[CH3:2].[CH3:57][C:58]([O:61][C:62]1[CH:67]=[CH:66][C:65]([CH2:68][C@H:69]([NH2:77])[C:70]([O:72]C(C)(C)C)=[O:71])=[CH:64][CH:63]=1)([CH3:60])[CH3:59].Cl.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:1]([NH:4][CH:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]([C:46](=[O:54])[C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([O:32][CH:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:31])=[C:19]([CH2:55][CH3:56])[CH:18]=1)[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:77][C@@H:69]([CH2:68][C:65]1[CH:64]=[CH:63][C:62]([O:61][C:58]([CH3:57])([CH3:59])[CH3:60])=[CH:67][CH:66]=1)[C:70]([OH:72])=[O:71])=[O:14])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16219019(S)-tert-Butyl 2-amino-3-(4-(tert-butoxy)phenyl)propanoate hydrochlorideHCID 222719565-{[2-(Acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoic acid

Product 1

HCID 86585322(2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoic acid (30 mg, 0.04 mmol), H-TYR(TBU)-OTBU HCL(26 mg, 0.08 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (16 mg, 0.048 mmol) and diisopropylethylamine (26 μL) in N,N-dimethylformamide (250 μL) was stirred at ambient temperature overnight, concentrated under reduced pressure and the residue purified by reverse-phase HPLC eluting with 5-100% acetonitrile/aqueous 0.1% trifluoroacetic acid to provide the titled compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue purified by reverse-phase
  3. washHPLC eluting with 5-100% acetonitrile/aqueous 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-d6060b51bd1647cda447d36f76e95216
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

Loading…