Isopropyl bromoacetate → 5-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-isopropoxycarbonyl-methyl ester

HRID 1416744Notes

Reaction equation

HRID 1416744 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[OH:29])[CH:9]([CH3:26])[CH2:10][C:11]1[CH:25]=[CH:24][C:14]2[O:15][C:16]([C:21]([OH:23])=[O:22])([C:18]([OH:20])=[O:19])[O:17][C:13]=2[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:38][C:39]([O:41][CH:42]([CH3:44])[CH3:43])=[O:40]>>[CH:42]([O:41][C:39]([CH:38]([O:19][C:18]([C:16]1([C:21]([OH:23])=[O:22])[O:15][C:14]2[CH:24]=[CH:25][C:11]([CH2:10][CH:9]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=3)[OH:29])[CH3:26])=[CH:12][C:13]=2[O:17]1)=[O:20])[C:6]([O:5][CH:1]([CH3:3])[CH3:2])=[O:7])=[O:40])([CH3:44])[CH3:43]

Participants

3

Reactant 2

HCID 121593Isopropyl bromoacetateHCID 538189185-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid

Product 1

HCID 545289815-(2-{tert-Butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-isopropoxycarbonyl-methyl ester

Procedure

The title compound was prepared from 5-(2-{tert-butoxycarbonyl-[2-(3-chloro-phenyl)-2-hydroxy-ethyl]-amino}-propyl)-benzo[1,3]dioxole-2,2-dicarboxylic acid and isopropyl 2-bromoacetate according to the procedure of Example 24, step 3 as a colorless oil: 1H NMR (300 MHz, CDCl3): δ 1.15-1.30 (m, 15H), 1.40 (s, 9H), 2.45-2.70 (m, 2H), 3.06-3.15 (m, 1H), 3.45-3.60 (m, 1H), 4.05-4.18 (m, 2H), 4.70-4.80 (m, 4H), 5.06 (sept, J=6.3 Hz, 2H), 5.46 (brs, 1H), 6.60-6.90 (m, 3H), 7.20-7.35 (m, 3H), 7.41 (s, 1H).; MS (ES) m/z (relative intensity): 722 (M+, 100).

Sources & evidence

ORD record
ord-99b0c12bc65446aa8e81236dc5b79e5f
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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