Propanal → HCID 10345099, compound

HRID 1294735Notes

Reaction equation

HRID 1294735 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([N:22]2[CH2:27][CH2:26][N:25](CCOC)[CH2:24][CH2:23]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH2:19][CH2:20][CH3:21])[CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].NC1C=C([C@H](N2CCN([CH2:62][CH2:63][CH2:64][O:65][CH3:66])CC2)C2C=CC(C(N(CC)CC)=O)=CC=2)C=CC=1.C(=O)CC.[B][B][B][B][B][B][B][B][B][B].C(O)(C(F)(F)F)=O>>[CH2:1]([N:3]([CH2:33][CH3:34])[C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([N:22]2[CH2:27][CH2:26][N:25]([CH2:62][CH2:63][CH2:64][O:65][CH3:66])[CH2:24][CH2:23]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][CH2:19][CH2:20][CH3:21])[CH:13]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 5

HCID 527PropanalHCID 6422Trifluoroacetic acidHCID 10252602HCID 10252602, compoundHCID 10389834HCID 10389834, compoundHCID 178419135HCID 178419135, compound

Product 1

HCID 10345099HCID 10345099, compoundYield 55%

Procedure

Using the same method as for COMPOUND 61 and using COMPOUND 60 (86.0 mg, 0.20 mmol), propionaldehyde (0.014 mL, 0.19 mmol) and decaborane (7.2 mg, 0.059 mmol) afforded COMPOUND 62 (89 mg, 55% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a hygroscopic, slightly yellow solid. Purity (HPLC): >97%; Optical purity (Chiral HPLC): >93%; 1H NMR (400 MHz, CD3OD) δ 1.01 (t, J=7.4 Hz, 3H), 1.09 (br t, J=6.6 Hz, 3H), 1.22 (br t, J=6.6 Hz, 3H), 1.70 (sextet, J=7.6 Hz, 2H), 1.95-2.04 (m, 2H), 2.39 (br s, 2H), 3.01 (br s, 2H), 3.15-3.28 (m, 8H), 3.33 (s, 3H), 3.45-3.61 (m, 6H), 4.55 (s, 1H), 7.10-7.16 (m, 1H), 7.34 (d, J=8.2 Hz, 2H), 7.37-7.44 (m, 3H), 7.57 (d, J=8.0 Hz, 2H). Found: C, 53.22; H, 6.76; N, 7.48. C29H44N4O2×2.0 H2O×2.0 CF3COOH has C, 53.22; H, 6.77; N, 7.52%. [α]D17=−1.5 deg [c 0.779, MeOH].

Sources & evidence

ORD record
ord-07719a522f8546109a78d6905d139e58
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

Loading…