Glycine methyl ester hydrochloride → HCID 57890114, compound

HRID 1819938Notes

Reaction equation

[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH:7]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[S:25][C:24]([CH:26]=O)=[C:23]([CH3:28])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:37][O:38][C:39](=[O:42])[CH2:40][NH2:41]>>[CH3:37][O:38][C:39](=[O:42])[CH2:40][NH:41][CH2:26][C:24]1[S:25][C:21]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:34])[CH3:35])[C:30]([CH3:31])([CH3:32])[CH3:33])=[C:11]([CH3:29])[CH:12]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:22][C:23]=1[CH3:28]

Participants

Reactant 2

HCID 122755Glycine methyl ester hydrochloride

HCID 57890162HCID 57890162, compound

Product 1

HCID 57890114HCID 57890114, compoundYield 64%

Procedure

Using a procedure analogous to Example 41, 5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-carbaldehyde (additional example Lu-13-A) (2.11 g, 4.09 mm) and glycine methyl ester hydrochloride (0.56 g, 4.50 mmol) give the title compound (1.54 g, 2.61 mmol, 64%). %). 1H NMR (CDCl3), δ 0.06 (s, 3H), 0.12 (s, 3H), 0.70 (t, J=6.9 Hz, 6H), 0.91(s, 9H), 0.97 (s, 9H), 2.02-2.10 (m, 4H), 2.13 (s, 3H), 2.20 (s, 3H), 3.45 (s, 2H), 3.67 (dd, J=5.4, 3.4 Hz, 1H), 3.73 (s, 3H), 3.82-3.87 (m, 3H), 3.98 (dd, J=9.6, 3.4 Hz, 1H), 6.49 (s, 1H), 6.67 (d, J=8.3 Hz, 1H), 7.00-7.05 (m, 2H). LC/MS (m/z): calcd for C33H55NO4SSi (M)+: 589.9; found: 589.0.

Sources & evidence

ORD record: ord-069d767a14ba4c31a7f8f709daf979ed
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601850B2

Reaction notes

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