Benzyl chloroformate → HCID 86599220, compound

HRID 2115991Notes

Reaction equation

HRID 2115991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C:5]2[O:9][CH:8]([CH2:10][NH2:11])[CH2:7][C:6]=2[CH:12]=1.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].C(N(C(C)C)CC)(C)C>>[CH2:22]([O:21][C:19](=[O:20])[NH:11][CH2:10][CH:8]1[CH2:7][C:6]2[CH:12]=[C:2]([Cl:1])[CH:3]=[C:4]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[C:5]=2[O:9]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960945HCID 11960945, compound

Product 1

HCID 86599220HCID 86599220, compoundYield 81%

Procedure

Treatment of (±)-(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylamine (2.45 g, 8.11 mmol) with benzyl chloroformate (2.07 g, 12.15 mmol) and diisopropylethylamine (3.43 g, 24.32 mmol) generally according to the procedure described for Intermediate 12 provided 2.6 g (81%) of (±)-benzyl(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a white solid. mp 90-92° C.; Anal. calcd. for C21H18ClNO3S: C, 63.07; H, 4.54; N, 3.50. Found: C, 63.44; H, 4.51; N, 3.43. Chiral HPLC separation of (±)-benzyl(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralpak AD, hexane:ethanol 1:1) provided two fractions. Fraction 1 (Rt=11.538 min, (Chiralpak AD, hexane:ethanol 1:1); Fraction 2 (Rt=17.694 min, (Chiralpak AD, hexane:ethanol 1:1).

Sources & evidence

ORD record
ord-37826cedbde94d1f82d28a64d503b7e9
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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