4-Ethylbenzaldehyde → HCID 10303660, compound

HRID 488940Notes

Reaction equation

C(N[C:6](=[O:37])[C@@H:7]([NH:19][C:20](=[O:36])[CH2:21][NH:22][C:23](=[O:35])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[NH2:34])[CH2:8][NH:9][CH2:10]C1C=CC(Br)=CC=1C)(C)(C)C.[CH2:38]([C:40]1[CH:47]=[CH:46][C:43](C=O)=[CH:42][CH:41]=1)[CH3:39]>>[CH2:38]([C:40]1[CH:41]=[CH:42][C:43]([CH2:10][NH:9][CH2:8][C@H:7]([NH:19][C:20](=[O:36])[CH2:21][NH:22][C:23](=[O:35])[C:24]2[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[CH:26][C:25]=2[NH:34][C:20]([NH:19][CH:7]([CH3:8])[CH3:6])=[O:36])[C@@H:6]([OH:37])[CH2:23][CH2:24][CH3:25])=[CH:46][CH:47]=1)[CH3:39]

Participants

Reactant 2

HCID 208614-Ethylbenzaldehyde

HCID 10281881HCID 10281881, compound

Product 1

HCID 10303660HCID 10303660, compound

Procedure

The compound 1.2 (Z=—C(O)—, R2=2-(isopropylaminocarbonyl)amino-5-(trifluoromethyl)phenyl, all other R=H; cf. procedure (65a); 0.93 g, 2.67 mmol) and (2S, 3S)-11.5 (l=m=0, PGN=CbzHN, R=propynyl, all other R=H; cf. procedure (68a); 1.0 g, 2.76 mmol) were combined in procedure (1c). A portion (52 mg, 0.11 mmol) of the resultant product was combined with 4-ethylbenzaldehyde (0.015 mL, 0.11 mmol) and taken through procedure (1d). The crude product was purified by RP-HPLC to afford the title compound (1S, 2S)-1.5 (l=m=0, R1=4-ethylphenyl, R3=—CH(OH)n-propyl, Z=—C(O)—, R2=2-(isopropylaminocarbonyl)amino-5-(trifluoromethyl)phenyl, all other R=H; 20 mg). Exact MS calcd for C29H41F3N5O4, the formula for (M+H)+=580.3111. Found: 580.3131.

Workup

customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-e7f2a0f25707437ca813a26e583479a3
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974836B2

Reaction notes

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