Methyl bromoacetate → HCID 70153021, compound

HRID 2187079Notes

Reaction equation

[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:10](=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](O)[CH:8]=2)[N:3]1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][CH2:28]1.Br[CH2:48][C:49]([O:51][CH3:52])=[O:50]>>[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:10](=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:48][C:49]([O:51][CH3:52])=[O:50])[CH:8]=2)[N:3]1[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([O:33][CH:34]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][CH2:28]1

Participants

Reactant 2

HCID 60984Methyl bromoacetate

HCID 17795944HCID 17795944, compound

Product 1

HCID 70153021HCID 70153021, compoundYield 72.2%

Procedure

Using the method similar to that in Example 106 and starting from ethyl 2,4-dioxo-1-[4-(4-diphenylmethoxypiperidino)butyl]-6-hydroxy-1,2,3,4-tetrahydroquinazoline-3-valerate (1.31 g, 2.09 mmol) obtained in Example 105, and also using methyl bromoacetate (237 ml, 2.50 mmol) instead of benzyl bromide, the ethyl ester of the title compound (990 mg, 68%) was obtained as an oil.

Sources & evidence

ORD record: ord-6e51b02af97b434481c0945cd2044124
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407116B1

Reaction notes

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