Triethylamine → HCID 86588818, compound

HRID 1633850Notes

Reaction equation

HRID 1633850 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:24]([O:31][C:32]([NH:34][C@@H:35]([C:38](O)=[O:39])[CH2:36][OH:37])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][N:16]([C:36](=[O:37])[C@@H:35]([CH2:38][OH:39])[NH:34][C:32]([O:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 489184Z-D-Ser-OHHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23505584HCID 23505584, compound

Product 1

HCID 86588818HCID 86588818, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

According to the procedure of Preparation 4(c), except using tert-butyl 4-fluoro-3-(benzylaminomethyl)benzoate (4.80 g, 15.2 mmole), N-(benzyloxycarbonyl)-D-serine (3.83 g, 16 mmole), HOBt H2O (2.16 g, 16 mmole), Et3N (2.24 mL, 16 mmole), EDC.HCl (3.07 g, 16 mmole), and 1:1 DMF/CH2Cl2 (75 mL), the title compound (1.58 g, 19%) was prepared as a thick oil following flash chromatography on silica gel (40% EtOAc/hexanes): 1H NMR (300 MHz, DMSO-d6) mixture of amide rotamers δ 7.39-8.18 (m, 2 H), 7.18-7.37 (m, 11 H), 4.25-5.11 (m, 7 H), 3.33-4.04 (m, 2 H), 1.53 (s, 9 H).

Sources & evidence

ORD record
ord-5062e63d83574e94b1a5f13128e2cc8b
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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