Acetic Acid → HCID 19388525, compound

HRID 1757513Notes

Reaction equation

HRID 1757513 reaction equation
[C:1](Br)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(=[O:25])C.CCCCC[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][NH2:39]>O1CCOCC1>[C:1]([NH:39][C:38](=[O:25])[C:37]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11692BromotriphenylmethaneHCID 13583DodecylamineHCID 4311764Sodium borohydride

Product 1

HCID 19388525HCID 19388525, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

R-(+)-prolinamide, 11, was converted to R-(+)-N-trilyl prolinamine, 12, using the procedure published in the literature (Hogberg, T., et al., Acta. Chem. Scand. 43, 660-664 (1989)), but using trityl bromide instead of trityl chloride. Compound 12 was reduced to R-(-)-B-trityl prolinamide,13, using sodium borohydride, acetic acid and dioxane. (Florvall, L., et al., J. Med. Chem. 25, 1280-86 (1982). The amine 12 was condensed with theacid 5 on the same basis as the synthesis of compound 6, to afford N-tritylbenzamide (14). Compound 14 was treated with hydrogen chloride in ethanol to give 15 in 65% yield. [α]D =-8.4° C. (C=1.4, MeOH), m.p. 200°-202° C. (hydrochloride salt), FT-IR (KBr) λ3390 (br, NH), 3300 (sharp, NH (amide)), 1660 (strong, C=O). 1H NMR (CDCI3) δ8.29 (br, NH), 7.95 (d, 1 H, J=1.95 Hz), 7.25 (d, 1H, J=1.99 Hz), 3.90 (s, 3H), 3.84 (s, 3H), 3.57 (m, 1H), 3.47 (m, 1H), 3.39 (m, 1H), 3.00 (m, 2H), 1.93 (m, 1H), 1.83 (m, 1H), 1.78 (m, 1H), 1.50 (m, 1H). Anal. calcd, for C14H20CIIO3N: C, H, N. Optical purity=100% retention time 8.75 mL (chiralcel OD, 10% ethanol/hexane, 1 mL/min).

Workup

  1. customcondensed with theacid 5 on the same basis

Sources & evidence

ORD record
ord-6b728adaa9d84ee3b32dad96def96d63
Source dataset
uspto-grants-1995_08
Patent number
US05446147

Reaction notes

Loading…