D-Cysteine → HCID 11101284, compound

HRID 1033396Notes

Reaction equation

[NH2:1][C@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][CH2:3]1.N[C@@H](C(O)=O)CS.[C:21]([O:25][C:26]([NH:28][C:29]([CH3:35])([CH3:34])[CH2:30][C:31](O)=[O:32])=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26]([NH:28][C:29]([CH3:35])([CH3:34])[CH2:30][C:31]([NH:1][C@H:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][CH2:3]1)=[O:32])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

Reactant 3

HCID 92851D-Cysteine

HCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid

HCID 109104143(S)-amino-3,4-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 11101284HCID 11101284, compound

Procedure

Prepared from 3(S)-amino-3,4-dihydro-1,5-benzothiazepin-4(5H)-one (prepared from D-cysteine (S-cysteine) by the method of Slade, et al, J. Med. Chem., 28, 1517-1521 (1985)) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (Example 31, Step E) by the procedure described in Example 1, Step F. 1H NMR (200 MHz, CDCl3): 1.38 (s,6H), 1.45 (s,9H), 2.32 (d,10 Hz, 1H), 2.50 (d,14 Hz, 1H), 2.70 (d,14 Hz, 1H), 2.92 (T,11 Hz, 1H), 3.93 (dd;7,11 Hz; 1H), 4.76 (m,1H), 7.02 (d,8 Hz, 1H), 7.1-7.3 (m,2H), 7.40 (t,8 Hz, 1H), 7.66 (d,7 Hz, 1H), 8.23 (br s,1H). FAB-MS: calculated for C19H27N3O4S 393; found 394 (M+H,36%).

Sources & evidence

ORD record: ord-fcf28a9737c345ec9a7376979519c0fe
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05310737

Reaction notes

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