Diisopropylcarbodiimide → HCID 66864948, compound

HRID 709466Notes

Reaction equation

HRID 709466 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NC(C)C)(C)C.[CH2:28]([O:35][C:36](=[O:49])[C@@H:37]([O:46][CH2:47][CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][C:42](O)=[CH:41][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.C(#N)C>[CH2:28]([O:35][C:36](=[O:49])[C@@H:37]([O:46][CH2:47][CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:17][C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:14][CH:13]=2)=[CH:41][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 66864807(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

Product 1

HCID 66864948HCID 66864948, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (4-tert-butoxycarbonylamino-phenyl)-acetic acid (100 mg, 0.39 mmol), N,N′-diisopropylcarbodiimide (60 mg, 0.47 mmol) and DMAP (15 mg, 0.12 mmol) in dry acetonitrile (15 mL) was added (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (120 mg, 0.39 mmol). The mixture was stirred for 3 h at r.t. before the solvent was evaporated and the remaining crude product directly purified by HPLC. The title compound was obtained as a solid (48 mg, 22.6%). 1H NMR (400 MHz, CDCl3): δ 7.25-7.36 (m, 9H), 7.16-7.18 (d, 2H), 6.91-6.93 (d, 2H), 5.12 (s, 2H), 4.00-4.03 (dd, 1H), 3.77 (s, 2H), 3.55-3.29 (m, 1H), 3.30-3.36 (m, 1H), 2.97-2.99 (m, 2H), 1.51 (s, 9H), 1.11-1.14 (t, 3H).

Workup

  1. customwas evaporated
  2. customthe remaining crude product directly purified by HPLC

Sources & evidence

ORD record
ord-007dfe7ea9c14afd8c6202fbae2d16db
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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