Water → HCID 57920995, compound

HRID 2266933Notes

Reaction equation

HRID 2266933 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([O:16][CH3:17])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].CC1C=CC(S(O)(=O)=O)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][NH:18][C:10](=[O:12])[C@@H:9]1[CH2:13][C@@H:14]([O:16][CH3:17])[CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

9

Reactant 7

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 409140Benzyl glycinateHCID 15222287(4R)-1-(tert-Butoxycarbonyl)-4-methoxy-L-proline

Product 1

HCID 57920995HCID 57920995, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Boc-Mop-OH (0.42 g, 1.71 mmol), H-Gly-OBn.TsOH (0.64 g, 1.88 mmol), DCC (0.35 g, 1.71 mmol), HOBt.H2O (0.26 g, 1.71 mmol) and DIEA (0.89 mL, 5.13 mmol) in DMF (30 mL) was stirred at room temperature under Ar(g) for 20 h. The mixture was filtered to remove insoluble DCU and concentrated by rotary evaporation under high vacuum. The product was isolated by flash chromatography (two columns were needed; the first was run in 8:2 EtOAc/hexanes and the second in 7:3 EtOAc/hexanes) affording Boc-Mop-Gly-OBn (0.55 g, 82%) as a clear oil. 1H NMR (500 MHz, CDCl3, ˜3:2 ratio of 2 rotamers): δ7.41-7.32 (m, 5 H), 6.53 (app bs, 0.4 H), 5.22-5.15 (m, 2 H), 4.44 (dd, J=7.9, 5.6 Hz, 0.6 H); 4.31 (t, J=7.8 Hz, 0.4 H), 4.16-3.97 (m, 2.6 H), 3.93 (app bs, 0.4 H), 3.81-3.72 (m, 0.6 H), 3.53-3.43 (m, 1.4 H), 3.32 and 3.31 (overlapping s, 3 H), 2.49-2.42 (m, 0.6 H), 2.41-2.33 (m, 0.4 H), 2.16-2.05 (m, 1 H), 1.89 (bs, 0.6 H), 1.47 (s, 5 H), 1.42 (s, 4 H);

Workup

  1. filtrationThe mixture was filtered
  2. customto remove insoluble DCU
  3. concentrationconcentrated by rotary evaporation under high vacuum
  4. customThe product was isolated by flash chromatography (two columns

Sources & evidence

ORD record
ord-f406b5f59db44e61895a1cb4f31ff91c
Source dataset
uspto-grants-2010_12
Patent number
US07858741B2

Reaction notes

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