HCID 68604720, compound → HCID 69363083, compound

HRID 2267668Notes

Reaction equation

O=C1NC2C=CC=CC=2S[C@H](C2C=CC=CC=2)[C@@H]1NC(=O)[C@H](C)NC(=O)CC1C=CC=CC=1.Br.[NH2:35][C@H:36]1[C:42](=[O:43])[NH:41][C:40]2[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=2[S:38][C@H:37]1[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.[F:54][C:55]1[CH:56]=[C:57]([CH2:62][C:63]([NH:65][C@H:66]([C:77](O)=[O:78])[CH2:67][C:68]2[NH:69][C:70]3[C:75]([CH:76]=2)=[CH:74][CH:73]=[CH:72][CH:71]=3)=[O:64])[CH:58]=[C:59]([F:61])[CH:60]=1>>[F:61][C:59]1[CH:58]=[C:57]([CH2:62][C:63]([NH:65][C@H:66]([C:77]([NH:35][C@@H:36]2[C:42](=[O:43])[NH:41][C:40]3[CH:44]=[CH:45][CH:46]=[CH:47][C:39]=3[S:38][C@@H:37]2[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:78])[CH2:67][C:68]2[NH:69][C:70]3[C:75]([CH:76]=2)=[CH:74][CH:73]=[CH:72][CH:71]=3)=[O:64])[CH:56]=[C:55]([F:54])[CH:60]=1

Participants

Reactant 3

HCID 68604720HCID 68604720, compound

HCID 68605990HCID 68605990, compound

HCID 68606034HCID 68606034, compound

Product 1

HCID 69363083HCID 69363083, compound

Procedure

A method similar to the one described for (97) was used except that (2,3-cisS)-3-amino-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide (9d) (105 mg) was used as the amine component and N-[(3,5-difluorophenyl)acetyl]-3-(1H-indol-2-yl)-L-alanine (110b) (119 mg) was used as the acid component to afford the title compound as a 1:1 mixture with the 2S,3S diastereomer (173 mg), white solid, m.p. 85-90° C. 1H NMR (300 MHz, d6-DMSO) δ 2.40 (m, 2H), 3.03 (m, 4H), 4.26 (m, 1H), 4.72 (m, 1H), 5.17 (d, 1H, J=7 Hz), 5.82 (d, 1H, J=6 Hz), 6.89-7.79 (m, 12H), 8.21 (m, 1H), 10.53 (m, 1H). MS APCI, m/z=611(M+1). LC/MS: 2.66 min.

Sources & evidence

ORD record: ord-696b71a5179b496c8ac0d5e2b879740a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858776B2

Reaction notes

Loading…