Triethylamine → HCID 9908289, compound

HRID 233754Notes

Reaction equation

HRID 233754 reaction equation
[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28](OCC2C=CC=CC=2)=O)[S:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([C:8]1[N:9]=[C:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH3:28])[S:11][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 22868967HCID 22868967, compound

Product 1

HCID 9908289HCID 9908289, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-5-(4-Benzyl-1,3-thiazol-2-yl)-3-(N-benzyloxycarbonylpyrrolidin-2-yl-methyl)-1 H-indole was used. Chromatography using 5% triethylamine in ethyl acetate afforded the title compound (71%) as a white solid: top, 146.0°-148.0° C.; 13C NMR (CDCl3) 67 169.8, 157.1, 139.3, 137.3, 129.2, 128.5, 128.0, 126.4, 125.7, 123.2, 121.2, 117.6, 114.8, 113.2, 111.5, 66.6, 57.5, 40.8, 38.1, 31.4, 29.6, 21.9; LRMS (m/z, relative intensity) 387 (M+, 4), 303 (34), 155 (30), 147 (17), 115 (18), 85 (63), 84 (100), 83 (57); [α]25 =+68° (CHCl3, c=1.0). Anal. calcd. for C24H25N3S·1/4H2O: C, 73.54; H, 6.56; N, 10.72. Found: C, 73.50; H, 6.53; N, 10.57.

Sources & evidence

ORD record
ord-71aeea3111504611916b554b3ea10e2e
Source dataset
uspto-grants-1997_01
Patent number
US05594014

Reaction notes

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