4-Bromoanisole → HCID 58487963, compound

HRID 1677796Notes

Reaction equation

HRID 1677796 reaction equation
CC1(C)[O:6][C@@H:5]([C@@H:7]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:8]([OH:10])=O)[C:4](=[O:22])O1.[OH:24][NH:25]C(=O)[C@@H](O)[C@@H](C(N1CCN(C2SN=C(C3C=CC=CC=3)N=2)CC1)=O)CC(C)C.BrC1C=CC(OC)=CC=1.[CH2:63]([CH:66]1[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]1)[CH2:64][CH3:65]>>[OH:24][NH:25][C:4](=[O:22])[C@@H:5]([OH:6])[C@H:7]([C:8]([N:69]1[CH2:70][CH2:71][CH:66]([CH2:63][CH2:64][CH3:65])[CH2:67][CH2:68]1)=[O:10])[CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 77304-BromoanisoleHCID 311694-PropylpiperidineHCID 11604459HCID 11604459, compoundHCID 67335259HCID 67335259, compound

Product 1

HCID 58487963HCID 58487963, compound

Procedure

The title product was prepared following the procedure of Example 64 (step a and b) but starting from (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-5-(4-methoxyphenyl)pentanoic acid (prepared following the procedure of Intermediate 2 but using 4-bromoanisole in step b) and 4-propylpiperidine (Aldrich). Purification by reverse-phase chromatography gave the title product as a yellow powder. M−(ESI): 405.4; M+(ESI): 407.4. HPLC (Condition A): Rt: 3.6 min (HPLC purity: 94.9%).

Workup

  1. customThe title product was prepared
  2. customprepared
  3. customPurification by reverse-phase chromatography

Sources & evidence

ORD record
ord-0addbd6703d14ec5b21fa64c99c6cd04
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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