Trifluoroacetic acid → Temocapil

HRID 256064Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]([NH:15][CH:16]1[CH2:22][S:21][CH:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:19][N:18]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:17]1=[O:36])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4]([CH:6]([NH:15][CH:16]1[CH2:22][S:21][CH:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:19][N:18]([CH2:28][C:29]([OH:31])=[O:30])[C:17]1=[O:36])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 13854109HCID 13854109, compound

Product 1

HCID 5393Temocapil

Procedure

Following the procedure described in Example 43, 0.3 g of isomer B of t-butyl α-[6-(1-ethoxycarbonyl-3-phenylpropylamino)-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [obtained as described in Example 49(h)], was de-t-butyrated using trifluoroacetic acid to afford the desired product as a crystalline powder in a yield of 83 mg. The product softened at about 135° C. and melted at 168° C.

Sources & evidence

ORD record: ord-4d87dad4470a4fe59c94d41c5dbebadb
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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