HCID 68604104, compound → HCID 10347665, compound

HRID 2267665Notes

Reaction equation

HRID 2267665 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:71](O)=[O:72])[CH2:67][CH2:68][S:69][CH3:70])=[O:64])[CH:58]=[C:59]([F:61])[CH:60]=1>>[F:54][C:55]1[CH:56]=[C:57]([CH2:62][C:63]([NH:65][C@H:66]([C:71]([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:72])[CH2:67][CH2:68][S:69][CH3:70])=[O:64])[CH:58]=[C:59]([F:61])[CH:60]=1

Participants

4

Reactant 3

HCID 68604104HCID 68604104, compoundHCID 68605990HCID 68605990, compoundHCID 68606034HCID 68606034, compound

Product 1

HCID 10347665HCID 10347665, compound

Procedure

A method similar to the one described for (97) was used except that (2,3-cis)-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]-L-methionine (109b) (91 mg) was used as the acid component to afford the title compound as a 1:1 mixture with the (2S,3S) diastereomer (63 mg), white solid, m.p. 85-90° C. 1H NMR (300 MHz, d6-DMSO) δ 1.55 (m, 4H), 2.20 (s, 3H), 2.40 (m, 12H), 3.03 (m, 4H), 4.26 (m, 1H), 4.72 (m, 1H), 5.17 (d, 1H, J=7 Hz), 5.829 (d, 1H, j=6 Hz), 6.89-7.79 (m, 12H), 8.21 (m, 1H), 10.53 (m, 1H). MS APCI, m/z=556(M+1). LC/MS: 2.55 min.

Sources & evidence

ORD record
ord-cf178f7f205c4554ad6b031bf9b7c57a
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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