HCID 18513400, compound → HCID 68781880, compound

HRID 2266934Notes

Reaction equation

HRID 2266934 reaction equation
C([O:8][C:9](=[O:45])[CH2:10][NH:11][C:12](=[O:44])[C@@H:13]1[CH2:17][C@@H:16]([O:18][CH3:19])[CH2:15][N:14]1[C:20](=[O:43])[C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:26]([O:28][CH2:29][CH:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])C1C=CC=CC=1.C(Cl)Cl.CO.CCO>CO.[Pd]>[CH:32]1[C:31]2[CH:30]([CH2:29][O:28][C:26]([N:22]3[CH2:23][CH2:24][CH2:25][C@H:21]3[C:20]([N:14]3[CH2:15][C@H:16]([O:18][CH3:19])[CH2:17][C@H:13]3[C:12]([NH:11][CH2:10][C:9]([OH:45])=[O:8])=[O:44])=[O:43])=[O:27])[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 18513400HCID 18513400, compoundHCID 68784821HCID 68784821, compound

Product 1

HCID 68781880HCID 68781880, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of Fmoc-Pro-Mop-Gly-OBn (0.74 g, 1.21 mmol) and Pd/C (0.07 g) in MeOH (25 mL) was stirred under an atmosphere of H2 (g) for 2 h. The mixture was filtered through a pad of Celite® and evaporated leaving a white solid. The product was isolated by flash chromatography (9:1 CH2Cl2/MeOH-EtOH) affording Fmoc-Pro-Mop-Gly-OH (0.54 g, 86%) as a white solid. 1H NMR (500 MHz, DMSO-d6, ˜1:1 ratio of 2 rotamers): δ7.91-7.82 (m, 2 H), 7.65 (t, J=7.4 Hz, 1 H), 7.58 (d, J=7.4 Hz, 0.5 H), 7.55 (d, J=7.5 Hz, 0.5 H), 7.44-7.28 (m, 5 H), 4.60 (dd, J=8.6, 3.1 Hz, 0.5 H), 4.52 (dd, J=8.6, 2.7 Hz, 0.5 H), 4.45-4.40 (m, 0.5 H), 4.34 (app t, J=7.4 Hz, 0.5 H), 4.27-4.10 (m, 3 H), 4.04-3.97 (m, 1 H), 3.76-3.70 (m, 0.5 H), 3.67-3.57 (m, 1.5 H), 3.42-3.29 (signals under H2O peak), 3.22 (s, 1.5 H), 3.11 (s, 1.5 H), 2.32-2.29 (m, 0.5 H), 2.28-2.18 (m, 0.5 H), 2.17-2.06 (m, 1.5 H), 2.02-1.73 (m, 4.5H); 13C NMR (125 MHz, DMSO-d6, ˜1:1 ratio of 2 rotamers): δ171.7, 171.0, 170.3, 170.2, 153.8, 143.9 (3 signals), 143.8, 140.7, 140.6, 127.7 (2 signals), 127.2, 127.1, 125.3, 125.1, 120.1, 120.0 (2 signals), 78.6, 78.4, 66.8, 66.5, 58.3 (2 signals), 57.9, 57.6, 56.1, 56.0, 55.9, 51.3, 51.2, 47.0, 46.7, 46.6, 46.3, 42.0, 34.3, 29.6, 28.6, 23.7, 22.6;

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. customevaporated
  3. customleaving a white solid

Sources & evidence

ORD record
ord-93ca08d730f640468a7cb8aba1e5613c
Source dataset
uspto-grants-2010_12
Patent number
US07858741B2

Reaction notes

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