DL-Phenylalaninol → HCID 18610528, compound

HRID 256040Notes

Reaction equation

C1C=CC(CC(N)CO)=CC=1.[CH2:12]([C@@H:19]1[N:25]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24](=[O:34])[C@@H:23]([NH:35][C@@H:36]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:22][S:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([C@@H]1N(CC(OC(C)(C)C)=O)C(=O)[C@@H](N[C@H](C(OCC)=O)CCC2C=CC=CC=2)CSC1)C1C=CC=CC=1>>[CH2:12]([C@@H:19]1[N:25]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[C:24](=[O:34])[C@@H:23]([NH:35][CH:36]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:22][S:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 76652DL-Phenylalaninol

HCID 18610529HCID 18610529, compound

HCID 18610530HCID 18610530, compound

Product 1

HCID 18610528HCID 18610528, compound

Procedure

The procedure described in steps (a) to (h) of Example 1 was repeated, except that L-2-amino-3-phenyl-1-propanol was used as the starting material. Two isomers (derived from the asymmetric carbon atom to which the phenethyl group is attached), that is t-butyl α-{3(S)-benzyl-6(R)-[1(R)-ethoxycarbonyl-3-phenylpropylamino]-5-oxoperhydro-1,4-thiazepin-4-yl}acetate (isomer A) and t-butyl α-{3(S)-benzyl-6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxoperhydro-1,4-thiazepin-4-yl}acetate (isomer B) were obtained as oils.

Workup

customwere obtained as oils

Sources & evidence

ORD record: ord-5e002efdff444940bf08e4d8950a0639
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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