HCID 23000581, compound → HCID 59038209, compound

HRID 1058224Notes

Reaction equation

C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[CH2:13][NH2:14])=O)(C)(C)C.C(OC([NH:27][C@@H:28]([C:36]([N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40](O)=[O:41])=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=O)(C)(C)C>>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][C@H:28]([C:36]([N:38]1[CH2:45][CH2:44][CH2:43][C@H:39]1[C:40]([NH:14][CH2:13][C:12]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=1[CH2:10][CH2:9][NH2:8])=[O:41])=[O:37])[NH2:27]

Participants

Reactant 2

HCID 23000581HCID 23000581, compound

HCID 69656260HCID 69656260, compound

Product 1

HCID 59038209HCID 59038209, compound

Procedure

The title compound was prepared from 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl amine from Step 4 and N-(tert-butoxycarbonyl)-3-pyridin-2-yl-D-alanyl-L-proline from Step 5 using a similar coupling, deprotection, and purification procedures as described in Steps 7 and 8 of Example 15: 1H NMR (DMSO-d6, 400 MHz): δ 8.84 (t, 1H, J=5.8 Hz), 8.72-8.62 (br m, 4H), 8.12-8.00 (br m, 4H), 7.54 (d, 2H, J=7.9 Hz), 7.33-7.19 (m, 4H), 4.58 (br s, 1H), 4.40-4.20 (m, 3H), 3.88-3.80 (m, 2H), 3.43-3.28 (m, 3H), 2.96 (br s, 4H), 1.90-1.75 (br m, 2H); MS (Electrospray): M+H=430.2; TLC Rf=0.13 (80/10/1 of methylene chloride/methanol/concentrated ammonium hydroxide).

Workup

customa similar coupling, deprotection, and purification procedures

Sources & evidence

ORD record: ord-241ca3b02ef844298da99cd40749b281
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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