Chlorosulfonyl isocyanate → 9H-Fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate

HRID 2120732Notes

Reaction equation

HRID 2120732 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C:23]4[CH:24]=[CH:25][C:26]([C:28]5[N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:30]=[CH:31][CH:32]=5)=[CH:27][C:22]=4[C:21]([CH3:41])([CH3:40])[O:20][CH:19]3[CH3:42])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClS([N:47]=[C:48]=O)(=O)=O>>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C:23]4[CH:24]=[CH:25][C:26]([C:28]5[N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:30]([C:48]#[N:47])=[CH:31][CH:32]=5)=[CH:27][C:22]=4[C:21]([CH3:41])([CH3:40])[O:20][CH:19]3[CH3:42])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 183745569H-fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate

Product 1

HCID 234355889H-Fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylateYield 65%

Procedure

Using the procedure for Example 18, the title compound (0.8 g, 65%) was prepared from 9H-fluoren-9-ylmethyl-6-[1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1 (4H)-carboxylate (1.2 g, 2.1 mmol) and chlorosulfonyl isocyanate (0.28 mL, 3.1 mmol). A white solid: mp 135-136° C.; 1H-NMR (DMSO-d6) δ 7.90 (t, 2H, J=6.7 Hz), 7.64 (d, 1H, J=7.5 Hz), 7.59 (d, 1H, J=7.1 Hz), 7.40 (td, 2H, J=7.2, 2.0 Hz), 7.31-7.34 (m, 3H), 7.29 (d, 1H, J=1.2 Hz), 7.04-7.09 (m, 2H), 6.44 (d, 1H, J=3.57 Hz), 5.30 (q, 1H, J=5.6 Hz), 4.86 (dd, 1H, J=10.7, 5.2 Hz), 4.64 (dd, 1H, J=10.8, 5.2 Hz), 4.33 (t, 1H, J=4.7 Hz). 1.50 (s, 3H), 1.30 (s, 9H), 1.20 (s, 3H), 1.03 (d, 3H, J=5.6 Hz); MS (ESI) m/z 590 [M+H]+.

Sources & evidence

ORD record
ord-a2cfc8681e2d492585ae1bd9eefd9f16
Source dataset
uspto-grants-2004_02
Patent number
US06693103B2

Reaction notes

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