1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Tert-butyl{2-[[(7r)-11-({[(3-chloropropyl)sulfonyl]amino}carbonyl)-14-cyclohexyl-7,8-dihydro-6h-indolo[1,2-e][1,5]benzoxazocin-7-yl](methyl)amino]ethyl}carbamate

HRID 498996

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].CCN=C=NCCCN(C)C.Cl.[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][N:31]([CH3:60])[C@@H:32]1[CH2:39][N:38]2[C:40]3[CH:41]=[C:42]([C:53](O)=[O:54])[CH:43]=[CH:44][C:45]=3[C:46]([CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]3)=[C:37]2[C:36]2[CH:56]=[CH:57][CH:58]=[CH:59][C:35]=2[O:34][CH2:33]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:53]([C:42]1[CH:43]=[CH:44][C:45]2[C:46]([CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)=[C:37]3[C:36]4[CH:56]=[CH:57][CH:58]=[CH:59][C:35]=4[O:34][CH2:33][C@H:32]([N:31]([CH3:60])[CH2:30][CH2:29][NH:28][C:26](=[O:27])[O:25][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:39][N:38]3[C:40]=2[CH:41]=1)=[O:54])(=[O:7])=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

3-chloropropane-1-sulfonamide (1.8 eq), DMAP (2.9 eq) and EDAC.HCl (1.8 eq) were added to a solution of (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid (prepared as described in Example 1, Step 7) (0.025 M) in DCM. The reaction was stirred under N2 at 40° C. for 2 h, before being allowed to cool. Volatiles were removed in vacuo to leave the crude product as a yellow gum which could be taken on without further purification. (ES+) m/z 687 (M+H)+; 689 (M+H)+

Workup

temperatureto cool
customVolatiles were removed in vacuo

Sources & evidence

ORD record: ord-6e2891af88c8405a8066f9dcaf946a3e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767660B2

Linked notes

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